Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions

Moaz M. Abdou; Rasha A. El-Saeed; Mohamed A. Abozeid; Mahmoud G. Sadek; E. Zaki; Y. Barakat; H. Ibrahim; Mahmoud Fathy; S. Shabana; M. Amine; Samir Bondock

doi:10.1016/j.arabjc.2015.11.004

View/Download PDF

Buy Reprints

PDF

Translate this page into:

Review

12 (

); 464-475

doi:

10.1016/j.arabjc.2015.11.004

Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions

Moaz M. Abdou^{^a,^d,⁎}, Rasha A. El-Saeed^{^b}, Mohamed A. Abozeid^{^b}, Mahmoud G. Sadek^{^b}, E. Zaki^{^a}, Y. Barakat^{^a}, H. Ibrahim^{^a}, Mahmoud Fathy^{^a}, S. Shabana^{^a}, M. Amine^{^a}, Samir Bondock^{^b,^c}

a Egyptian Petroleum Research Institute, Nasr City, P.O. 11727, Cairo, Egypt

b Department of Chemistry, Faculty of Science, Mansoura University, ET-35516 Mansoura, Egypt

c Department of Chemistry, Faculty of Science, King Khalid University, 9004 Abha, Saudi Arabia

d The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan

⁎Corresponding author. Tel.: +20 1000409279. moaz.chem@gmail.com (Moaz M. Abdou)

Received: 2015-7-8, Accepted: 2015-11-8, Published: 2015-05-01

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

The preparation and the properties of the elusive tetronic acid are reviewed, including its synthesis, chemical reactivity and reactions.

Keywords

Tetronic acid

Synthetic routes

Chemical reactivity

Tautomeric structure

Reactions

Show Related Articles from PubMed

1 Introduction

Tetronic acids, 4-hydroxy-2(5H)-furanones, were discovered in 1896 by Wolffe and Schwabe (1896). They are a structural fragment of a series of natural compounds, such as acetogenins, muconolactones, leptosfaerin, and strigol (Cain et al., 1989; De Guzman and Schnutz, 1990; Iida et al., 1997; Miller and Hegedus, 1993; Miller et al., 1998; Ribbons and Sutherland, 1994; Rupprecht et al., 1990; Schiehser et al., 1986; Tejedor and García-Tellado, 2004; Zografos and Georgiadis, 2006 ). They represent an interesting template for medicinal chemistry because of their antibiotic (Brodersen and Kjaer, 1946; Capon and MacLeod, 1987; Haynes and Plimmer, 1960; Ley et al., 1991; Matsumoto et al., 1990; Vanwagenen and Cardellina, 1986; Vieweg et al., 2014 ), HIV-1 protease inhibitors (Roggo et al., 1994), anticoagulant (Rehse and Emisch, 1983; Rehse and Rothe, 1982; Rehse et al., 1978; Witiak et al., 1982 ), antiepileptic (Zhang et al., 1992), antibacterial (Murray et al., 2014), antifungal (Luk and Readshaw, 1991; Vishwakarma et al., 1987; Hu et al., 2014 ), insecticidal (Ibi et al., 1979), analgesic (Dal Pozzo et al., 1974) and anti-inflammatory activities (Foden et al., 1975). Recently, these compounds have also been reported as anticancer agents (Andreoli et al., 2014; Han et al., 2014; kamal et al., 2014a, 2014b ).

In continuation of our studies in exploring the utilization of cyclic 1,3-dicarbonyl compounds as versatile precursors for synthesis of organic compounds (Abdou et al., 2015, 2019; Abdou, 2017a, 2017b, 2017c, 2018; Metwally et al., 2013a, 2013b, 2012a, 2012b, 2012c, 2012d, 2012e ). The aim of this review was to give an account of the principal literature on methods of synthesis and the reactivity of tetronic acid (without any substituents attached). The discussion is supported by numerous lucid diagrams and the extensive reaction schemes are supported by relevant and up-to-date references from the original literature.

2 Tautomeric structure(s)

Tetronic acid can exist in either the keto- or enol-form (Fig. 1). These four possible prototropic transformations have been intensively examined by various chemical reactivity, spectral, thermochemical, and computational methods (Ballantine et al., 1968; Duncanson, 1953; Edsall and Sagall, 1943; Haynes et al., 1968; Jurd, 1996; Martoglio and Katon, 1993; Pollet et al., 1984; Zimmer et al., 1978 ).

Possible tautomeric structures of tetronic acid 1 (A–D).

3 Synthesis

The syntheses of tetronic acid are reported throughout the literature (Allan et al., 1983; Bloomer and Kappler, 1976; Greenhill et al., 1975; Greenhill and Tomassini, 1974; Haynes and Plimmer, 1960; Pollet and Gelin, 1978; Schmidt and Zimmer, 1981; Svendsen and Boll, 1973 ; Zimmer et al., 1978), although very little has been done to concentrate the wide range of syntheses into a single report.

3.1

3.1 Using 1, 3-dioxin-4-one

Sato et al. (1990) disclosed a simple and inexpensive synthesis of tetronic acid 1 in 78% yield via refluxing of 6-(hydroxymethyl)-dioxin-4-one 2 in toluene (Scheme 1).

3.2

3.2 Using lactonization of γ-acetoxy-β-keto esters

Gelin and Pallet (1980) reported that the desired tetronic acid 1 could be obtained by lactonization of γ-acetoxy-β-keto ester 3 in refluxing toluene (Scheme 2).

3.3

3.3 Debromination of α-bromotetronic

A catalytic debromination of α-bromotetronic 4 with palladium on carbon, under approximately 40 lbs of hydrogen pressure, results in 90% yield of 1 (Schmidt and Zimmer, 1981) (Scheme 3).

4 Chemical reactions

In this section, all the reactions with participation of tetronic acid on the basis of the new bond formed.

4.1

4.1 Reactions involving carbon–carbon bond formation

4.1.1

4.1.1 C–C bond formation reactions

4.1.1.1

4.1.1.1 C₃-alkylation

Ramachary and Kishor (2010) observed that the reaction of tetronic acid 1 with benzaldehyde 6 and diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 7 under proline catalysis in dichloromethane gave 3-benzyl-tetronic acid 8 (Scheme 4).

Michael addition reactions of 1 to β-nitroalkenes 9 afforded 3-(1-substituted-2-nitro-ethyl)-furan-2,4-diones 10. This reaction requires a basic catalyst in organic solvents, as well as long reaction times, which may lead to environmentally hazardous residues and undesirable by-products (Iwata et al., 1993). Recently, an environmentally benign, fast and convenient protocol for this reaction by a grinding method under catalyst and solvent-free conditions was reported (Xie et al., 2012) (Scheme 5).

The double alkylation of tetronic acid 1 with 1,1-disubstituted alkenes 11 in the presence of manganese(III) acetate in acetic acid at room temperature afforded the diethyl- and/or ethenyl-ethyl-substituted tetronic acids 12 and/or 13 along with peroxypropellane 14 (Haque and Nishino, 2011) (Scheme 6).

4.1.1.2

4.1.1.2 C₃-allylation reaction

The allylation of 1 is an important strategy for the formation of C–C bonds in organic synthesis. Activator-free and one-pot C-allylation of 1 by simple palladium catalyst in water using cinnamyl alcohol 15 and heating gave the corresponding C-allylated product 16 (Gan et al., 2008; Shue and Yang, 2012) (Scheme 7).

Prat et al. (1988) reported that tetronic acid 1 is efficiently alkylated with cinnamyl acetate 17 to afford 16 (38%) using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), palladium(II) 2,4-pentanedionate, triphenylphosphine as catalyst in tetrahydrofuran (Scheme 8).

The above methodology (Moreno-Mañas et al., 1988; Prat et al., 1988) was successfully applied for the alkylation by using 2-cyclohexenyl acetate 18. This reaction proceeds smoothly to give the corresponding monoalkylated lactone 19 (57%) although minor amounts of the dialkylated butanolide 20 were also isolated (Scheme 9).

Tetronic acid 1 was dialkenylated with allyl bromide 21 under the phase-transfer catalyst [e.g., benzyltriethylammonium chloride (Kotha and Deb, 2008) or tetra(n-butyl)ammonium hydrogensulfate (Kotha et al., 2005)] to give a mixture of C-diallylated tetronic acid 22 and O-allylated isomer 23 [83] (Scheme 10).

4.1.1.3

4.1.1.3 C₃-benzylation

Jurd (1997, 1996) reported that the reaction of tetronic acid 1 with Mannich bases 24 in acetic acid furnished benzyl lactones 25 (Scheme 11).

4.1.1.4

4.1.1.4 Arylation

An efficient palladium-catalyzed cross-coupling reaction of tetronic acid 1 with arylboronic acid 26 in the presence of palladium dichloride in tetrahydrofuran at 60 °C afforded 2(5H)-furanones 27 in good yields (Hu et al., 2011) (Scheme 12).

4.1.1.5

4.1.1.5 Olefination

A most frequently used method for constructing 3-arylmethylenetetrahydrofuran-2,4-diones 29 is the Knoevenagel condensation between tetronic acid 1 and several substituted benzaldehydes 28 under reflux (Chen et al., 2011; Kozlov et al., 2008; Pashkovskii et al., 2008 ) (Scheme 13).

The microwave assisted condensation reaction of aldehydes 28 with tetronic acid 1 on acidic Montmorillonite KSF gave efficiently 3-(arylmethylene)-2,4-(3H,5H)furandiones 30 (Villemin and Labiad, 1990) (Scheme 14).

Heating tetronic acid 1 and triethyl orthoformate 31 for two hours gave 3-ethoxymethylene-3H-2,4-dione 32 in 60% yield (Otto, 1987) (Scheme 15).

4.1.1.6

4.1.1.6 Allylindation

Yonemitsu-type trimolecular condensation of 1 with indole 33 and propanal 34 was promoted by TiCl₄, afforded 2-(indol-3-yl)-2-(2-propyl)tetronic acid 35 (Gérard et al., 2010) (Scheme 16).

Colombo et al. (2008) developed a three-component domino allylindation reaction of 1H-indole-3-carbaldehyde 36 with allyl bromide 37 and 1 in the presence of indium metal in a mixture of tetrahydrofuran and water (1:1) afforded the desired adduct 38 (Scheme 17).

4.1.1.7

4.1.1.7 Acetylation reaction

C-acylation of tetronic acid 1 with aliphatic carboxylic acids 39 in the presence of N,N′-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) in dichloromethane gave 3-acyltetrahydrofuran-2,4-diones 40 (Baati et al., 2011, 2010; Nomura et al., 1986; Pashkovskii et al., 2003; Rouleau et al., 2013; Murray et al., 2014 ) (Scheme 18).

4.2

4.2 Reactions involving carbon–heteroatom bond formation

4.2.1

4.2.1 C–N bond formation

4.2.1.1

4.2.1.1 Coupling reactions

3-Arylazotetronic acids 42 were prepared by coupling of 1 with diazotized arylamines 41 in aqueous sodium hydroxide solution (Tanaka et al., 1984) (Scheme 19).

4.2.1.2

4.2.1.2 Nitration reaction

Nitration of 1 with concentrated nitric acid in diethyl ether afforded 3-nitrotetronic acid 43 (Pollet et al., 1984) (Scheme 20).

4.2.1.3

4.2.1.3 Amination reaction

Reaction of tetronic acid 1 with an equimolar amount of various anilines 44 produced the corresponding 3-anilinolactones 45 in excellent yields (Cole et al., 2002; Cook et al., 1994; Darwish et al., 2004; Ghahremanzadeh et al., 2013; Jeedimalla et al., 2013; Madec et al., 2008; Momose et al., 1988; Paulvannan and Stille, 1994; Savina et al., 2007; Shaabani et al., 2010 ) (Scheme 21).

The condensation reaction of tetronic acid 1 with o-phenylenediamines 46 at different reaction conditions (YCl₃, AcOH, EtOH) gave 4-(2-aminophenylamino)furan-2(5H)-ones 47 (Amari et al., 2002; Bentarzi et al., 2009; Cai et al., 2011; Cheng et al., 2011; Kaoua et al., 2013 ) (Scheme 22).

4.2.1.4

4.2.1.4 Diazotization reactions

Regitz reaction using p-toluenesulfonyl azide (TsN₃) as the diazo transfer reagent remains the most efficient approach despite it is hampered by potential hazard and purification problems to remove the p-tosylamide co-product (Chapman et al., 1987; Geraghty et al., 2000). Even, 2-azido-3-ethylbenzthiazolium tetrafluoroborate was revealed as an effective diazo transfer reagent for the transformation of 1 into 3-diazotetrahydrofuran-2,4-dione 48 (Stachel et al., 1994) (Scheme 23).

4.2.2

4.2.2 C–S bond formation

4.2.2.1

4.2.2.1 Sulfonation reaction

Combs et al. (2005) showed that sulfonation of 1 with sodium hydrogensulfite in ethanol resulted in the formation of the corresponding sulfonic acid 49 (Scheme 24).

4.2.2.2

4.2.2.2 Thionation reaction

Treatment of 1 with Lawesson’s reagent 50 in boiling toluene afforded the regioselective thiolotetronic acid 51 in 70% yield (Desbene-Finck et al., 2006) (Scheme 25).

Goddard et al. (2010) have reported that treatment of 1 with Martin’s sulfurane 52, in diethyl ether afforded the corresponding sulfur ylide 53 in 73% yield (Scheme 26).

4.2.3

4.2.3 C–O bond formation

4.2.3.1

4.2.3.1 Esterification

Radical precursors, enol esters 55, were prepared by coupling of 2-bromobenzoic acids 54 with tetronic acid 1 in the presence of 2-chloro-1-methylpyridinium iodide and triethylamine in THF at room temperature (Pugh et al., 2003; Zhang, 2000) (Scheme 27).

In addition, O-acylation of tetronic acid 1 with pivaloyl chloride 56 in the presence of 4-dimethylaminopyridine (DMAP) (Axelrod et al., 2013) or 4- pyrrolidinopyridine (Balthazor, 1992) afforded 2,2-dimethyl-2,5-dihydro-5-oxo-3-furanyl ester 57 (Scheme 28).

4.2.3.2

4.2.3.2 O-alkylation reaction

O-alkyl tetronic acids are compounds of interest, being useful starting materials for natural product synthesis (Hamada and Shiori, 1984; Kametani et al., 1987, 1986; Schmidt et al., 1983 ). Many methods for the O-alkylation of tetronic acids have been reported in the literature. However, most of the reported methods are restricted to form the methyl and ethyl tetronates using alkylating agents such as dimethyl or diethyl sulfate (Wegnel et al., 1979), trimethyloxonium tetraflouroborate (Wegnel et al., 1979) and diazomethane (Ley and Wadsworth, 1989). The Fischer etherification method (Gelin and Pallet, 1980) was used successfully for the preparation of methyl and ethyl tetronates.

Zimmer et al. (1988) studied the preparation of alkyl tetronates by treatment of primary or secondary alcohols and tetronic acid with conc. H₂SO₄. Although this procedure allows for preparation of various alkyl ethers, it has some serious limitations.

Hoffmann et al. (1989) have reported a modification of Zimmer’s method which replaces the excess of conc. H₂SO₄ with a catalytic amount of p-toluenesulfonic acid. While this modification works well with primary alcohols, secondary alcohols gave poor yields of the alkyl tetronate.

Treatment of tetronic acid 1 with an alkyl bromides or with alcohols 58 under Mitsunobu conditions [diisopropyl diazenedicarboxylate (DIAD)] (Bach and Kemmler, 2003; Bajwa and Anderson, 1990; Billaud et al., 2007 ) represents a general method for the regio-specific O-alkylation of tetronic acid 59 in high yields. Alternatively, cesium fluoride (CsF) in dimethylformamide (DMF) has been reported to be an efficient agent for the O-alkylation of tetronic acid (method B) (Bach et al., 2004) (Scheme 29).

4.2.3.3

4.2.3.3 Sulfonates ether formation

Several groups have developed general methodology for the one step formation of 61 via tosylation reaction of tetronic acid 1 with tosyl chloride 60 in the presence of triethylamine at room temperature (Blanc et al., 2013; Sun et al., 2005; Wang et al., 2003 ) (Scheme 30).

The compound 1 was readily converted to the corresponding triflates 63 in 66% yield by treatment with triflic anhydride 62 in methylene chloride in the presence of N,N-diisopropylethylamine (DIPEA) (Grigg et al., 1997, 1994) (Scheme 31).

4.2.3.4

4.2.3.4 Phosphorylation reaction

4-Phosphonium trifluoromethanesulfonate 65 was generated in situ by the reaction of tetronic acid 1 with triphenylphosphonium anhydride trifluoromethanesulfonate (Hendrickson’s reagent) 64 (Paintner et al., 2003) (Scheme 32).

4.2.4

4.2.4 Carbon–halogen bond formation

Halogenoheteroarenes are useful intermediates for the syntheses of bioactive natural products and pharmaceutical drugs.

4.2.4.1

4.2.4.1 Bromination

Bromination of tetronic acid 1 with oxalyl bromide in dichloromethane and DMF at room temperature yielded 4-bromo-5H-2-furanone 66 (Boukouvalas and Albert, 2011; Bach et al., 2012; Barrett et al., 2006; Brecker et al., 1999; Jas, 1991; Xin et al., 2000 ) (Scheme 33).

When the bromination of 1 is carried out using N-bromosuccinimide (NBS) as effective promoters in ethanol at room temperature, it afforded 2-bromotetronic acid 184 (Ge and Kirk, 1997) (Scheme 34).

5 Conclusion

We hope to have conveyed to the readers of this review the current interest of the synthetic community in the synthesis, and chemical reactivity of tetronic acid. It seems likely that this review will serve as a useful reference for chemists interested in discovering new types of reactions and synthesis of tetronic acid.

References

Abdou M.M., El-Saeed R.A., Bondock S., . Recent advances in 4-hydroxycoumarin chemistry. Part 2: scaffolds for heterocycle molecular diversity. Arab. J. Chem. 2015
[CrossRef] [Google Scholar]
Abdou M.M., . 3-Acetyl-4-hydroxycoumarin: synthesis, reactions and applications. Arab. J. Chem.. 2017;10(Suppl. 2):S3664-S3675.
[Google Scholar]
Abdou M.M., . Chemistry of 4-hydroxy-2(1H)-quinolone. Part 1: synthesis and reactions. Arab. J. Chem.. 2017;10(Suppl. 2):S3324-S3337.
[Google Scholar]
Abdou M.M., . Utility of 4-hydroxythiocoumarin in organic synthesis. Arab. J. Chem.. 2017;10(Suppl. 2):S3955-S3961.
[Google Scholar]
Abdou M.M., . Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arab. J. Chem.. 2018;11(7):1061-1071.
[Google Scholar]
Abdou M.M., El-Saeed R.A., Bondock S., . Recent advances in 4-hydroxycoumarin chemistry. Part 1: synthesis and reactions. Arab. J. Chem.. 2019;12(1):88-121.
[Google Scholar]
Allan R.D., Johnston G.A., Kazlauskas R., Tran H.W., . Synthesis of analogues of γ-aminobutyric acid. Part 11. Unsaturated and saturated tetronic acid [furan-2, 4 (3H, 5H)-dione] derivatives. J. Chem. Soc. Perkin. 1983;I:2983-2985.
[Google Scholar]
Boukouvalas J., Albert V., . Synthesis of the hypoxic signaling inhibitor furospongolide. Synlett.. 2011;17:2541-2544.
[Google Scholar]
Paintner F.F., Allmendinger L., Bauschke G., . Highly efficient 4-O-alkylations of tetronic acids involving oxyphosphonium intermediates. Synlett. 2003;1:83-86.
[Google Scholar]
Amari M., Fodili M., Nedjar-Kolli B., Hoffmann P., Perie J., . Reactivity studies on 4-aminopyrones: access to benzimidazole and benzimidazolone derivatives. J. Heterocyclic Chem.. 2002;39(4):811-816.
[Google Scholar]
Andreoli M., Persico M., Kumar A., Orteca N., Kumar V., Pepe A., Fattorusso C., . Identification of the first inhibitor of the GBP1: PIM1 interaction. Implications for the development of a new class of anticancer agents against paclitaxel resistant cancer cells. J. Med. Chem.. 2014;57(19):7916-7932.
[Google Scholar]
Axelrod A., Chin M.R., Eliasen A.M., Siegel D., Zlotkowski K., . Synthesis of xanthofulvin and vinaxanthone, natural products enabling spinal cord regeneration. Angew. Chem. Int. Ed. Engl.. 2013;52(12):3421-3424.
[Google Scholar]
Baati R., Ghobril C., Kister J.A., . Synthetic route to α-substituted butenolides: enantioselective synthesis of (+)-ancepsenolide. Eur. J. Org. Chem.. 2011;19:3416-3419.
[Google Scholar]
Baati R., Goncalves S., Wagner A., Nicolas M., . Exploring the one-pot C-acylation of cyclic 1,3-diones with unactivated carboxylic acid. Tetrahedron Lett.. 2010;51(17):2348-2350.
[Google Scholar]
Bach T., Fort D.A., Knust H., Nettekoven M., Woltering T.J., . Synthesis of fluorinated tricyclic scaffolds by intramolecular [2+2] photocycloaddition reactions. Angew. Chem. Int. Ed. Engl.. 2012;51(40):10169-10172.
[Google Scholar]
Bach T., Kemmler M., . [2+2] Photocycloaddition of tetronates. Angew. Chem. Int. Ed. Engl.. 2003;42(39):4824-4826.
[Google Scholar]
Bach T., Kemmler M., Herdtweck E., . Inter- and intramolecular [2+2]-photocycloaddition of tetronates – stereoselectivity, mechanism, scope and synthetic applications. Eur. J. Org. Chem.. 2004;22:4582-4595.
[Google Scholar]
Bajwa J.S., Anderson R.C., . Regiospecific o-alkylation of β-tetronic acids under mitsunobu reaction conditions. Tetrahedron Lett.. 1990;31(48):6973-6976.
[Google Scholar]
Ballantine J.A., Fenwick R.G., Ferrito V., . The fragmentation of tetronic acids and related compounds under electron-impact. Org. Mass Spectrom.. 1968;1(6):761-775.
[Google Scholar]
Balthazor W., . Diels-alder chemistry of a 2,4-dioxygenated furan. Synth. Commun. 1992:1023-1026.
[Google Scholar]
Barrett A.G.M., Le Vezouet R., White A.J.P., Burrows J.N., . Synthetic studies on the CDEF ring system of lactonamycin. Tetrahedron. 2006;62(52):12252-12263.
[Google Scholar]
Bentarzi Y., Hammal L., Nedjar-Kolli B., Hoffmann P., . Synthesis of tetracyclic pyrano[4,3-b]-6H-imidazo[1,2-a] [1,5]benzodiazepines. Heterocycl. Commun.. 2009;15(3):209-215.
[Google Scholar]
Billaud C., Bodio E., Bourdreux Y., Gall T.L., Mioskowski C., Willis C., . Flexible synthesis of vulpinic acids from tetronic acid. Tetrahedron Lett.. 2007;48(37):6421-6424.
[Google Scholar]
Blanc A., Cheval N.P., Dikova A., Pale P., Weibel J., . Vinyl nosylates: an ideal partner for palladium-catalyzed cross-coupling reactions. Chem.-Eur. J.. 2013;19(27):8765-8768.
[Google Scholar]
Bloomer J.L., Kappler F.E., . Microbial metabolites. Part XI. Total synthesis and absolute configuration of (S)-carlosic acid (4-butyryl-2,5-dihydro-3-hydroxy-5-oxo-furan-2-acetic acid) and conversion of (R)-5-methyltetronic acid into (R)-carolic acid {3,4-dihydro-8-methylfuro [3,4-b] oxepin-5,6 (2H, 8H)-di-one} J. Chem. Soc., Perkin Trans.. 1976;1(14):1485-1491.
[Google Scholar]
Brecker L., Kreiser W., Ernst L., Hopf H., Brecker L., . 3-Bromo-2,5-dihydrofuran-2-one and 4-bromo-2,5-dihydrofuran-2-one. Collect. Czech. Chem. Commun.. 1999;64(7):1154-1158.
[Google Scholar]
Brodersen R., Kjaer A., . The antibacterial action and toxicity of some unsaturated lactones. Acta Pharmacol. Toxicol.. 1946;2:109-120.
[Google Scholar]
Cai L., Ji X.S., Qi X., Fan Y.Z., . Efficient synthesis of functionalized benzimidazoles and perimidines: ytterbium chloride catalyzed C–C bond cleavage. Chin. J. Chem.. 2011;29(9):1880-1886.
[Google Scholar]
Cain R.B., Freer A.A., Kirby G.W., Rao G.V., . Resolution of (±)-3-methylmuconolactone and the absolute configurations of the naturally occurring 3-and 4-methylmuconolactones: X-ray crystal structures of (S)-1-phenylethylammonium salts and a bromodilactone. J. Chem. Soc., Perkin Trans.. 1989;1(1):202-203.
[Google Scholar]
Capon R.J., MacLeod J.K., . A new sesterterpene tetronic acid from an Australian sponge, Ircinia sp. Aust. J. Chem.. 1987;40(7):1327-1330.
[Google Scholar]
Chapman O.L., Miller M.D., Pitzenberger S.M., . Infrared spectroscopy of matrix-isolated propadienone. J. Am. Chem. Soc.. 1987;109(22):6867-6868.
[Google Scholar]
Chen T., Benmohamed R., Arvanites A.C., Ranaivo H.R., Morimoto R.I., Ferrante R.J., Silverman R.B., . Arylsulfanyl pyrazolones block mutant SOD1-G93A aggregation. Potential application for the treatment of amyotrophic lateral sclerosis. Bioorg. Med. Chem. Lett.. 2011;19(1):613-622.
[Google Scholar]
Cheng C., Jiang B., Tu S., Li G., . [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives. Green Chem.. 2011;13(8):2107-2115.
[Google Scholar]
Cole K.P., Hahn J.M., Hsung R.P., McLaughlin M.J., Wang J.A., . A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(±)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones. Organic Lett.. 2001;4(12):2017-2020.
[Google Scholar]
Colombo F., Cravotto G., Palmisano G., Penoni A., Sisti M., . Three-component indium-mediated domino allylation of 1H-indole-3-carbaldehyde with electron-rich (hetero) arenes: highly efficient access to variously functionalized indolylbutenes. Eur. J. Org. Chem.. 2008;16:2801-2807.
[Google Scholar]
Combs A.P., Crawley M.L., McLaughlin E., Zhu W., . Concise approach to novel isothiazolidinone phosphotyrosine mimetics: microwave-assisted addition of bisulfite to activated olefins. Org. Lett.. 2005;7(22):5067-5069.
[Google Scholar]
Cook G.R., Beholz L.G., Stille J.R., . Construction of hydroxylated alkaloids (+/−)-mannonolactam, (+/−) deoxymannojirimycin, and (+/−)-prosopinine through aza-annulation. J. Org. Chem.. 1994;59(13):3575-3584.
[Google Scholar]
Dal Pozzo A., Dansi A., Neneghini E., . Unsaturated gamma-lactones. Relationship between their structure and antimicrobial activity. Bull. Chim. Farm.. 1974;113(5):280-324.
[Google Scholar]
Darwish O.S., Hahn J.M., Hsung R.P., Liu J., Sydorenko N., Hahn J.M., . Tetronamides as latent acyclic vinylogous amides in formal Aza-[3+3] cycloaddition reactions with α,β-unsaturated iminium salts. An unexpected rearrangement and an approach to synthesis of substituted piperidines. J. Org. Chem.. 2004;69(20):6732-6738.
[Google Scholar]
De Guzman F.S., Schnutz F.J., . Peroxy aliphatic esters from the sponge plakortis lita. J. Nat. Prod.. 1990;53:926-931.
[Google Scholar]
Desbene-Finck S., Giorgi-Renault S., Helissey P., Labruere R., . Efficient syntheses of thiono and dithio analogues of tetronic acid. Synthesis. 2006;24:4163-4166.
[Google Scholar]
Duncanson L.A., . Infra-red spectroscopy and structural chemistry. Part IV. The infra-red spectra of some tetronic acids. J. Chem. Soc. 1953:1207-1211.
[Google Scholar]
Edsall J.T., Sagall E.L., . Raman spectra of l-ascorbic acid, tetronic acid and related compounds. J. Am. Chem. Soc.. 1943;65(7):1312-1316.
[Google Scholar]
Foden F.R., McCormick J., O’Mant D.M., . Vulpinic acids as potential antiinflammatory agents. 1. Vulpinic acids with substituents in the aromatic rings. J. Med. Chem.. 1975;18(2):199-203.
[Google Scholar]
Gan K.H., Jhong C.J., Yang S.C., . Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water. Tetrahedron. 2008;64(7):1204-1212.
[Google Scholar]
Ge P., Kirk K.L., . Synthesis of 2-fluorotetronic acid. J. Fluorine Chem.. 1997;84(1):45-47.
[Google Scholar]
Gelin S., Pallet P., . Tetronic acids and derivatives part VIII (1) o-alkylation of 3-unsubstituted tetronic acids. Syn. Comm.. 1980;10(11):805-811.
[Google Scholar]
Geraghty N.W.A., Kennedy B.D., Murphy P.V., O’Sullivan T.J., . The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: benzofuran formation. J. Chem. Soc., Perkin Trans.. 2000;1(13):2121-2126.
[Google Scholar]
Gérard S., Renzetti A., Lefevre B., Fontana A., de Maria P., Sapi J., . Multicomponent reactions studies: yonemitsu-type trimolecular condensations promoted by Ti (IV) derivatives. Tetrahedron. 2010;66(16):3065-3069.
[Google Scholar]
Ghahremanzadeh R., Naeimi H., Rashid Z., Zarnani A.H., . Synthesis of novel spirooxindoles in water by using MnFe₂O₄ nanoparticles as an efficient magnetically recoverable and reusable catalyst. Appl. Catal.. 2013;467:270-278.
[Google Scholar]
Goddard R., Huang X., Maulide N., . A direct ylide transfer to carbonyl derivatives and heteroaromatic compounds. Angew. Chem. Int. Ed. Engl.. 2010;49(47):8979-8983.
[Google Scholar]
Greenhill J.V., Ramli M., Tomassini T., . Reduction of enaminones in the preparation of 3-aminocyclohexanols; a novel preparation of tetronic acid. J. Chem. Soc. Perkin Trans. 1. 1975;6:588-591.
[Google Scholar]
Greenhill J.V., Tomassini T., . A new and easier route to tetronic acid. Tetrahedron Lett.. 1974;15(31):2683-2684.
[Google Scholar]
Grigg R., Kennewell P., Savic V., . Palladium catalysed cross-coupling of vinyl triflates with 9-alkyl-9-borobicyclo[3,3,1]nonanes. Total synthesis of (−)-isoseiridine. Tetrahedron. 1994;50(18):5489-5494.
[Google Scholar]
Grigg R., Savic V., Thornton-Pett M., . 4-Substituted protoanemonin in intramolecular cycloaddition reactions of non-stabilised azomethine ylides. Tetrahedron. 1997;53(30):10633-10642.
[Google Scholar]
Hamada Y., Shiori T., . New methods and reagents in organic synthesis. 49. A highly efficient stereoselective synthesis of l-daunosamine through direct C-acylation using diphenyl phosphorazidate (DPPA) Tetrahedron Lett.. 1984;25(47):5409-5412.
[Google Scholar]
Han C., Zhang T., Zhang A., Wang D., Shi W., Tao J., . Efficient catalyst-free one-pot three-component synthesis of novel spiro-oxindole derivatives, and their cytotoxic activities. Synthesis. 2014;46(10):1389-1398.
[Google Scholar]
Haque M.A., Nishino H., . Synthesis of peroxylactones using Mn (III)-catalyzed aerobic oxidation. Heterocycles. 2011;83:1783-1805.
[Google Scholar]
Haynes L.J., Kirkien Konasiewicz A., Loudon A.G., Maccoll A., . The fragmentation of organic molecules under electron‐IMPACT—II. The mass spectra of tetronic acid and some of its derivatives. Org. Mass Spectrom.. 1968;1(6):743-759.
[Google Scholar]
Haynes L.J., Plimmer J.R., . Tetronic acids. Quart. Rev.. 1960;14:292-315.
[Google Scholar]
Hoffmann H.M.R., Schmidt B., Wolff S., . Preparation of 5-bromotetronates [4-alkoxy-5-bromo-2 (5H)-furanones] and a new concept for the synthesis of aflatoxins and related structure types. Tributyltin hydride versus palladium-promoted intramolecular hydroarylation. Tetrahedron. 1989;45(19):6113-6126.
[Google Scholar]
Hu Y., Ding Q., Ye S., Peng Y., Wu J., . Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C–OH bond activation. Tetrahedron. 2011;67(38):7258-7262.
[Google Scholar]
Hu Y., Wang J., Lu A., Yang C., . Synthesis, characterization, antifungal evaluation and 3D-QSAR study of phenylhydrazine substituted tetronic acid derivatives. Bioorg. Med. Chem. Lett.. 2014;24(16):3772-3776.
[Google Scholar]
Ibi A., Taniguchi E., Maekawa K., . Syntheses and biological activities of tetramic acid and tetronic acid derivatives [growth regulators] Agric. Biol. Chem.. 1979;43:1641-1646.
[Google Scholar]
Iida A., Kano M., Kubota Y., Koga K., Tomioka K., . Targeting DNA topoisomerase II with podophyllotoxin aza-analogue. Bioorg. Med. Chem. Lett.. 1997;7(20):2565-2566.
[Google Scholar]
Iwata S., Ishiguro Y., Utsugi M., Mitsuhashi K., Tanaka K., . 3,3,3-Trifluoro-1-nitropropene as a novel trifluoromethyl-containing building block. Bull. Chem. Soc. Jpn.. 1993;66(8):2432-2435.
[Google Scholar]
Jas G., . A simple resolution of 4-bromo-2-(tert-butyldimethylsiloxy)furan from tetrahydro-2,4-dioxofuran. Synthesis. 1991;11:965-966.
[Google Scholar]
Jeedimalla N., Johns J., Roche S.P., . Mechanistic investigation and implications of a sacrificial aniline for the tandem cascade synthesis of 4-aza-podophyllotoxin analogues. Tetrahedron Lett.. 2013;54(44):5845-5848.
[Google Scholar]
Jurd L., . New anti-tumor agents. 3. Phenolic benzopyran lactone and amine derivatives. J. Heterocyclic Chem.. 1997;34(2):601-604.
[Google Scholar]
Jurd L., . New anti-tumor agents heterocyclic benzodioxole lactones. J. Heterocyclic Chem.. 1996;33:1227-1232.
[Google Scholar]
Kamal A., Reddy T.S., Polepalli S., Paidakula S., Srinivasulu V., Reddy V.G., Shankaraiah N., . Synthesis and biological evaluation of 4-aza-2,3-dihydropyridophenanthrolines as tubulin polymerization inhibitors. Bioorg. Med. Chem. Lett.. 2014;24(15):3356-3360.
[Google Scholar]
Kamal A., Tamboli J.R., Nayak V.L., Adil S.F., Vishnuvardhan M.V.P.S., Ramakrishna S., . Synthesis of a terphenyl substituted 4-aza-2,3-didehydropodophyllotoxin analogues as inhibitors of tubulin polymerization and apoptosis inducers. Bioorg. Med. Chem.. 2014;22(9):2714-2723.
[Google Scholar]
Kametani T., Katoh T., Tsubuki M., Honda T., . Stereoselective synthesis of 26,27-bisnorbrassinolide. Chem. Pharm. Bull.. 1987;35(6):2334-2338.
[Google Scholar]
Kametani T., Katoh T., Tsubuki M., Honda T., . One-step stereochemical determination of four contiguous acyclic chiral centers on a steroidal side chain: a novel synthesis of brassinolide. J. Am. Chem. Soc.. 1986;108(22):7055-7060.
[Google Scholar]
Kaoua R., Kaoua R., Le Gal Y., Lorcy D., Roisnel T., Kaoua R., Nedjar-Kolli B., . Electroactive 1,5-benzodiazepines bearing either a tetrathiafulvalene or a ferrocene moiety. Tetrahedron. 2013;69(23):4636-4640.
[Google Scholar]
Kotha S., Deb A.C., . Design and synthesis of spiro-heterocycles by ring-closing metathesis. Indian J. Chem.. 2008;47(7):1120-1134.
[Google Scholar]
Kotha S., Deb A.C., Kumar R.V., . Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction. Bioorg. Med. Chem. Lett.. 2005;15(4):1039-1043.
[Google Scholar]
Kozlov N.G., Bondarev S.L., Kadutskii A.P., Basalaeva L.I., Pashkovskii F.S., . Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained. Russ. J. Org. Chem.. 2008;44(7):1031-1037.
[Google Scholar]
Ley S.V., Trudell M.L., Wadsworth D.J., . The total synthesis of agglomerin A and (±)-carolinic acid. A general method for the preparation of 3-acyl tetronic acids via direct acylation of O-methyl 3-stannyl tetronates. Tetrahedron. 1991;47(38):8285-8296.
[Google Scholar]
Ley S.V., Wadsworth D.J., . Preparation of O-methyl 3-acyl tetronic acids by the direct acylation of stannyl tetronates. Tetrahedron Lett.. 1989;30:1001-1004.
[Google Scholar]
Luk K., Readshaw S.A., . Structural studies of MM46115, a novel tetronic acid containing macrolide with antiviral and antibacterial activity isolated from Actinomadura pelletieri. J. Chem. Soc., Perkin Trans.. 1991;1(7):1641-1644.
[Google Scholar]
Madec D., Mingoia F., Prestat G., Poli G., . N-substituted tetronamides as ambident nucleophilic building blocks for the synthesis of new 4-aza-2,3-didehydropodophyllotoxins. Synlett. 2008;10:1475-1478.
[Google Scholar]
Martoglio P.A., Katon J.E., . The vibrational assignment of tetronic acid. J. Mol. Struct.. 1993;296(1):35-51.
[Google Scholar]
Matsumoto M., Kawamura Y., Yoshimura Y., Terui Y., Nakai H., Yoshida H.I., Shoji I., . Isolation, characterization and structures of PA-46101 A and B. J. Antibiot.. 1990;43(7):739-747.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . A facile synthesis, tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes. Color. Technol.. 2013;129(6):418-424.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . A worthy insight into the dyeing applications of azo pyrazolyl dyes. Int. J. Modern Org. Chem.. 2012;1(3):165-192.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Pyrazol-5-ones: tautomerism, synthesis and reactions. Int. J. Modern Org. Chem.. 2012;1(1):19-54.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, structure investigation and dyeing assessment of novel bisazo disperse dyes derived from 3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones for dyeing polyester fabrics. J. Korean Chem. Soc.. 2012;56(3):348-356.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, structure elucidation and application of some new azo disperse dyes derived from 4-hydroxycoumarin for dyeing polyester fabrics. Am. J. Chem.. 2012;2(6):347-354.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, tautomeric structure, dyeing characteristics, and antimicrobial activity of novel 4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones. J. Korean Chem. Soc.. 2012;56(1):82-91.
[Google Scholar]
Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, spectroscopic studies and technical evaluation of novel disazo disperse dyes derived from 3-(2-hydroxyphenyl)-2-pyrazolin-5-ones for dyeing polyester fabrics. Am. J. Chem.. 2013;3(4):59-67.
[Google Scholar]
Miller M., Hegedus L.S., . Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita. J. Org. Chem.. 1993;58(24):6779-6785.
[Google Scholar]
Miller T.A., Vachaspati P.R., Labroli M.A., Thompson C.D., Bulman A.L., Macdonald T.L., . The synthesis and evaluation of benzannelated-azatoxins: the benzazatoxins. Bioorg. Med. Chem. Lett.. 1998;8(9):1065-1070.
[Google Scholar]
Momose T., Toyooka N., Nishi T., Takeuchi Y., . (3H)- and 2(5H)-furanones. III. An efficient synthesis and the eschenmoser-mannich reaction of unsubstituted 4-amino-2(5H)-furanone. Heterocycles. 1988;27(8):1907-1924.
[Google Scholar]
Moreno-Mañas M., Prat M., Ribas J., Virgili A., . Palladium catalyzed allylic C-alkylation of highly acidic and enolic heterocyclic substrates: tetronic acid and triacetic acid lactone. Tetrahedron Lett.. 1988;29(5):581-584.
[Google Scholar]
Murray E.J., Crowley R.C., Truman A., Clarke S.R., Cottam J.A., Jadhav G.P., Steele V.R., O’Shea P., Lindholm C., Cockayne A., Chhabra S.R., Chan W.C., Williams P., . Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors. J. Med. Chem.. 2014;57(6):2813-2819.
[Google Scholar]
Nomura K., Hori K., Arai M., Yoshii E., . An efficient method for 3 (C)-acylation of tetronic acids. Chem. Pharm. Bull.. 1986;34(12):5188-5190.
[Google Scholar]
Otto W., . Nitrogen-containing derivatives of tetronic acid. Arch. Pharm.. 1987;320(8):749-755.
[Google Scholar]
Pashkovskii F.S., Katok Y.M., Khlebnikova T.S., Koroleva E.V., Lakhvich F.A., . Heterocyclic analogs of prostaglandins: I. Synthesis of 3-alkyl (aralkyl)-2,5-dihydrofuran-2-ones as synthons for 11-deoxy-10-oxaprostanoids. Russ. J. Org. Chem.. 2003;39(7):998-1009.
[Google Scholar]
Pashkovskii F.S., Shchukina E.M., Gribovskii M.G., Lakhvich F.A., . Heterocyclic analogs of prostaglandines: IV. Synthesis of 3,7-interphenylene 3,10 (11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes. Russ. J. Org. Chem.. 2008;44(5):657-670.
[Google Scholar]
Paulvannan K., Stille J.R., . Heterocycle formation through aza-annulation: stereochemically controlled syntheses of (+/−)-5-epitashiromine and (+/−)-tashiromine. J. Org. Chem.. 1994;59(7):1613-1620.
[Google Scholar]
Pollet P.L., Perzanowski H.P., Gelin S., . Tautomerism in 3-nitrotetronic acids. Spectrochim. Acta Mol. Biomol. Spectrosc.. 1984;40(11):1007-1009.
[Google Scholar]
Pollet P., Gelin S., . Tetronic acids and derivatives-IV: synthesis and lactonization of-γ-acetoxy β-ketoesters. Tetrahedron. 1978;34(10):1453-1455.
[Google Scholar]
Prat M., Moreno-Mañas M., Ribas J., . Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds. Tetrahedron. 1988;44(23):7205-7212.
[Google Scholar]
Pugh G., Zhang W., Zhang W., . Free radical reactions for heterocycle synthesis. Part 7: 2-bromobenzoic acids as building blocks in the construction of spirobenzolactones and spirobenzolactams. Tetrahedron. 2003;59(24):4237-4247.
[Google Scholar]
Ramachary D.B., Kishor M., . Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1, 5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions. Org. Biomol. Chem.. 2010;8(12):2859-2867.
[Google Scholar]
Rehse K., Emisch U., . Tetronsäuren mit direkten antikoagulanten Wirkungen. Arch. Pharm.. 1983;316(2):115-120.
[Google Scholar]
Rehse K., Rothe M., . Untersuchungen Zur Eiweißbindung Von Arzneistoffen Durch Kontinuierliche Ultrafiltration. 4. Mitt. Arch. Pharm.. 1982;315(3):259-262.
[Google Scholar]
Rehse K., Wagenknecht J., Rietbrock N., . Anticoagulant activity of 3,5-disubstituted tetronic acids. Arch. Pharm.. 1978;311(12):986.
[Google Scholar]
Ribbons D.W., Sutherland A.G., . (+)-Muconolactone from arene biotransformation in Pseudomonas putida: production, absolute configuration and enantiomeric purity. Tetrahedron. 1994;50(11):3587-3594.
[Google Scholar]
Roggo B.E., Petersen F., Delmendo R., Jenny H.B., Peter H.H., Roesel J., . 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin new inhibitors of HIV-1 protease. I. Fermentation isolation and biological activity. J. Antibiot.. 1994;47(2):136-142.
[Google Scholar]
Rouleau J., Korovitch A., Lion C., Hémadi M., Ha-Duong N.T., El Hage Chahine J.M., Le Gall T., . Synthesis and evaluation of 3-acyltetronic acid-containing metal complexing agents. Tetrahedron. 2013;69(51):10842-10848.
[Google Scholar]
Rupprecht J.K., Hui Y.H., McLaughlin J.L., . Annonaceous acetogenins: a review. J. Nat. Prod.. 1990;53(2):237-278.
[Google Scholar]
Sato M., Sakaki J.I., Takayama K., Kobayashi S., Suzuki M., Kaneko C., . A novel synthetic method for tetronic acids from 1,3-dioxin-4-ones via intra-or intermolecular ketene trapping. Chem. Pharm. Bull.. 1990;38(1):94-98.
[Google Scholar]
Savina S.A., Lyubchanskaya V.M., Alekseeva L.M., Shashkov A.S., Granik V.G., . Synthesis of novel furoquinolines and furobenzodiazepines from tetronic acid. Russ. Chem. Bull.. 2007;56(11):2298-2304.
[Google Scholar]
Schiehser G.A., White J.D., Matsumoto G., Pezzanite J.O., Clardy J., . The structure of leptosphaerin. Tetrahedron Lett.. 1986;27(46):5587-5590.
[Google Scholar]
Schmidt D.G., Seemuth P.D., Zimmer H., . Substituted. gamma.-butyrolactones. Part 31.2,4(3H,5H)-furandione: heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones. J. Org. Chem.. 1983;48(11):1914-1916.
[Google Scholar]
Schmidt D.G., Zimmer H.A., . Convenient synthesis of 2,4(3H, 5H)-furandione (β-tetronic acid) Synth. Commun.. 1981;11(5):385-390.
[Google Scholar]
Shaabani A., Sarvary A., Keshipour S., Rezayan A.H., Ghadari R., . Unexpected Knoevenagel self-condensation reaction of tetronic acid: synthesis of a new class of organic heterocyclic salts. Tetrahedron. 2010;66(10):1911-1914.
[Google Scholar]
Shue Y.J., Yang S.C., . Activator-free and one-pot C-allylation by simple palladium catalyst in water. Tetrahedron Lett.. 2012;53(11):1380-1384.
[Google Scholar]
Stachel H., Poschenrieder H., Redlin J., Schachtner J., Zeitler K., . Reductones of tetronic, thiotetronic and tetramic acids, II. Reductones by rhodium-catalyzed decomposition of diazo compounds. Liebigs Ann. Chem.. 1994;2:129-132.
[Google Scholar]
Sun X., Wu J., Zhang L., . Efficient route to 4-substituted-2 (5H)-furanones, 2 (1H)-quinolones, and pyrones by nickel-catalyzed cross-coupling of arenesulfonates with organozinc reagents. Chem. Lett.. 2005;34(6):796-797.
[Google Scholar]
Svendsen A., Boll P.M., . Naturally occuring lactones and lactames-V: halogenated β-keto esters as starting materials for the synthesis of tetronic acids. Tetrahedron. 1973;29(24):4251-4258.
[Google Scholar]
Tanaka K., Matsuo K., Nakanishi A., Jo M., Shiota H., Yamaguchi M., Kawaguchi K., . Syntheses and antimicrobial activities of five-membered heterocycles having a phenylazo substituent. Chem. Pharm. Bull.. 1984;32(8):3291-3298.
[Google Scholar]
Tejedor D., García-Tellado F., . Synthesis and chemistry of tetronic acids. Org. Prep. Proc. Int.. 2004;36(1):33-59.
[Google Scholar]
Vanwagenen B.C., Cardellina J.H. II, . Native american food and medicinal plants 7: antimicrobial tetronic acid from lomatium dissectum. Tetrahedron. 1986;42(4):1117-1122.
[Google Scholar]
Vieweg L., Reichau S., Schobert R., Leadlay P.F., Süssmuth R.D., . Recent advances in the field of bioactive tetronates. Nat. Prod. Rep.. 2014;31(11):1554-1584.
[Google Scholar]
Villemin D., Labiad B., . Clay catalysis: dry condensation of tetronic acid with aldehydes under microwave irradiation. Synthesis of 3-(arylmethylene)-2,4-(3H, 5H) furandiones. Synth. Commun.. 1990;20(20):3207-3212.
[Google Scholar]
Vishwakarma R.A., Kapil R.S., Popli S.P., . Studies in medicinal-plants. New lactones from hypericum-mysorense. Indian J. Chem.. 1987;26(5):486-487.
[Google Scholar]
Wang L., Wu J., Zhu Q., Fathi R., Yang Z., Yang Z., . Palladium-catalyzed cross-coupling reactions of 4-tosyl-2 (5H)-furanone with boronic acids: a facile and efficient route to generate 4-substituted 2 (5H)-furanones. J. Org. Chem.. 2003;68(2):670-673.
[Google Scholar]
Wegnel A.S., Reffstrup T., Boll P.M., . Regiospecific alkylation of tetronic acids: formation of 4-alkoxy-5H-furan-2-ones and 2-alkoxy-5H-furan-4-ones. Terrahedron. 1979;35(18):2181-2185.
[Google Scholar]
Witiak D.T., Kokrady S.S., Patel S.T., Akbar H., Feller D.R., Newman H.A., . Hypocholesterolemic and antiaggregatory properties of 2-hydroxytetronic acid redox analogs and their relationship to clofibric acid. J. Med. Chem.. 1982;25(1):90-93.
[Google Scholar]
Wolffe, L., Schwabe, C., 1896. Tetronic acid. Liebigs. J. Ann. Chem. 292, 231; Chem. Abstr., 70, I, 522–524.
Xie Z.B., Wang N., Wu M.Y., He T., Le Z.G., Yu X.Q., . Catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to nitroalkenes by a grinding method. Beilstein J. Org. Chem.. 2012;8(1):534-538.
[Google Scholar]
Xin Z., Zheng G.Z., Stewart A.O., . 2-Siloxy-4-furanyl anion: remarkable solvent effect on its nucleophilicity. Synlett. 2000;9:1324-1326.
[Google Scholar]
Zhang C.L., Chatterjee S.S., Stein U., Heinemann U., . Comparison of the effects of losigamone and its isomers on maximal electroshock induced convulsions in mice and on three different patterns of low magnesium induced epileptiform activity in slices of the rat temporal cortex. Naunyn-Schmideberg’s Arch. Pharmacol.. 1992;345(1):85-92.
[Google Scholar]
Zhang W., . Free radical reactions for heterocycle synthesis. Part 3: formation of novel spirodilactones, spirolactone-lactams, andes spirolactone-thiolactones. Tetrahedron Lett.. 2000;41(15):2523-2527.
[Google Scholar]
Zimmer H., Amer A., Pham C.V., Schmidt D.G., Zimmer H., Amer A., Van P.C., Schmidt D.G., . On the synthesis of 4-alkoxy-2 (5H)-furanones. J. Org. Chem.. 1988;53(14):3368-3370.
[Google Scholar]
Zimmer H., Hillstrom W.W., Schmidt J.C., Seemuth P.D., Vogeli R., . Substituted. gamma.-lactones. 28. 3-(phenylmethylene)-2,4-(3H, 5H) furandiones. J. Org. Chem.. 1978;43(8):1541-1544.
[Google Scholar]
Zografos A.L., Georgiadis D., . Synthetic strategies towards naturally occurring tetronic acids. Synthesis. 2006;19:3157-3188.
[Google Scholar]

Introduction

Tautomeric structure(s)

Synthesis

Using 1, 3-dioxin-4-one
Using lactonization of γ-acetoxy-β-keto esters
Debromination of α-bromotetronic

Chemical reactions

Reactions involving carbon–carbon bond formation
Reactions involving carbon–heteroatom bond formation

Conclusion

Fulltext Views
2,324

PDF downloads
1,060

View/Download PDF
Download Citations

BibTeX
RIS

Show Sections

[1] Abdou M.M., El-Saeed R.A., Bondock S., . Recent advances in 4-hydroxycoumarin chemistry. Part 2: scaffolds for heterocycle molecular diversity. Arab. J. Chem. 2015
[CrossRef] [Google Scholar]

[2] Abdou M.M., . 3-Acetyl-4-hydroxycoumarin: synthesis, reactions and applications. Arab. J. Chem.. 2017;10(Suppl. 2):S3664-S3675.
[Google Scholar]

[3] Abdou M.M., . Chemistry of 4-hydroxy-2(1H)-quinolone. Part 1: synthesis and reactions. Arab. J. Chem.. 2017;10(Suppl. 2):S3324-S3337.
[Google Scholar]

[4] Abdou M.M., . Utility of 4-hydroxythiocoumarin in organic synthesis. Arab. J. Chem.. 2017;10(Suppl. 2):S3955-S3961.
[Google Scholar]

[5] Abdou M.M., . Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arab. J. Chem.. 2018;11(7):1061-1071.
[Google Scholar]

[6] Abdou M.M., El-Saeed R.A., Bondock S., . Recent advances in 4-hydroxycoumarin chemistry. Part 1: synthesis and reactions. Arab. J. Chem.. 2019;12(1):88-121.
[Google Scholar]

[7] Allan R.D., Johnston G.A., Kazlauskas R., Tran H.W., . Synthesis of analogues of γ-aminobutyric acid. Part 11. Unsaturated and saturated tetronic acid [furan-2, 4 (3H, 5H)-dione] derivatives. J. Chem. Soc. Perkin. 1983;I:2983-2985.
[Google Scholar]

[8] Boukouvalas J., Albert V., . Synthesis of the hypoxic signaling inhibitor furospongolide. Synlett.. 2011;17:2541-2544.
[Google Scholar]

[9] Paintner F.F., Allmendinger L., Bauschke G., . Highly efficient 4-O-alkylations of tetronic acids involving oxyphosphonium intermediates. Synlett. 2003;1:83-86.
[Google Scholar]

[10] Amari M., Fodili M., Nedjar-Kolli B., Hoffmann P., Perie J., . Reactivity studies on 4-aminopyrones: access to benzimidazole and benzimidazolone derivatives. J. Heterocyclic Chem.. 2002;39(4):811-816.
[Google Scholar]

[11] Andreoli M., Persico M., Kumar A., Orteca N., Kumar V., Pepe A., Fattorusso C., . Identification of the first inhibitor of the GBP1: PIM1 interaction. Implications for the development of a new class of anticancer agents against paclitaxel resistant cancer cells. J. Med. Chem.. 2014;57(19):7916-7932.
[Google Scholar]

[12] Axelrod A., Chin M.R., Eliasen A.M., Siegel D., Zlotkowski K., . Synthesis of xanthofulvin and vinaxanthone, natural products enabling spinal cord regeneration. Angew. Chem. Int. Ed. Engl.. 2013;52(12):3421-3424.
[Google Scholar]

[13] Baati R., Ghobril C., Kister J.A., . Synthetic route to α-substituted butenolides: enantioselective synthesis of (+)-ancepsenolide. Eur. J. Org. Chem.. 2011;19:3416-3419.
[Google Scholar]

[14] Baati R., Goncalves S., Wagner A., Nicolas M., . Exploring the one-pot C-acylation of cyclic 1,3-diones with unactivated carboxylic acid. Tetrahedron Lett.. 2010;51(17):2348-2350.
[Google Scholar]

[15] Bach T., Fort D.A., Knust H., Nettekoven M., Woltering T.J., . Synthesis of fluorinated tricyclic scaffolds by intramolecular [2+2] photocycloaddition reactions. Angew. Chem. Int. Ed. Engl.. 2012;51(40):10169-10172.
[Google Scholar]

[16] Bach T., Kemmler M., . [2+2] Photocycloaddition of tetronates. Angew. Chem. Int. Ed. Engl.. 2003;42(39):4824-4826.
[Google Scholar]

[17] Bach T., Kemmler M., Herdtweck E., . Inter- and intramolecular [2+2]-photocycloaddition of tetronates – stereoselectivity, mechanism, scope and synthetic applications. Eur. J. Org. Chem.. 2004;22:4582-4595.
[Google Scholar]

[18] Bajwa J.S., Anderson R.C., . Regiospecific o-alkylation of β-tetronic acids under mitsunobu reaction conditions. Tetrahedron Lett.. 1990;31(48):6973-6976.
[Google Scholar]

[19] Ballantine J.A., Fenwick R.G., Ferrito V., . The fragmentation of tetronic acids and related compounds under electron-impact. Org. Mass Spectrom.. 1968;1(6):761-775.
[Google Scholar]

[20] Balthazor W., . Diels-alder chemistry of a 2,4-dioxygenated furan. Synth. Commun. 1992:1023-1026.
[Google Scholar]

[21] Barrett A.G.M., Le Vezouet R., White A.J.P., Burrows J.N., . Synthetic studies on the CDEF ring system of lactonamycin. Tetrahedron. 2006;62(52):12252-12263.
[Google Scholar]

[22] Bentarzi Y., Hammal L., Nedjar-Kolli B., Hoffmann P., . Synthesis of tetracyclic pyrano[4,3-b]-6H-imidazo[1,2-a] [1,5]benzodiazepines. Heterocycl. Commun.. 2009;15(3):209-215.
[Google Scholar]

[23] Billaud C., Bodio E., Bourdreux Y., Gall T.L., Mioskowski C., Willis C., . Flexible synthesis of vulpinic acids from tetronic acid. Tetrahedron Lett.. 2007;48(37):6421-6424.
[Google Scholar]

[24] Blanc A., Cheval N.P., Dikova A., Pale P., Weibel J., . Vinyl nosylates: an ideal partner for palladium-catalyzed cross-coupling reactions. Chem.-Eur. J.. 2013;19(27):8765-8768.
[Google Scholar]

[25] Bloomer J.L., Kappler F.E., . Microbial metabolites. Part XI. Total synthesis and absolute configuration of (S)-carlosic acid (4-butyryl-2,5-dihydro-3-hydroxy-5-oxo-furan-2-acetic acid) and conversion of (R)-5-methyltetronic acid into (R)-carolic acid {3,4-dihydro-8-methylfuro [3,4-b] oxepin-5,6 (2H, 8H)-di-one} J. Chem. Soc., Perkin Trans.. 1976;1(14):1485-1491.
[Google Scholar]

[26] Brecker L., Kreiser W., Ernst L., Hopf H., Brecker L., . 3-Bromo-2,5-dihydrofuran-2-one and 4-bromo-2,5-dihydrofuran-2-one. Collect. Czech. Chem. Commun.. 1999;64(7):1154-1158.
[Google Scholar]

[27] Brodersen R., Kjaer A., . The antibacterial action and toxicity of some unsaturated lactones. Acta Pharmacol. Toxicol.. 1946;2:109-120.
[Google Scholar]

[28] Cai L., Ji X.S., Qi X., Fan Y.Z., . Efficient synthesis of functionalized benzimidazoles and perimidines: ytterbium chloride catalyzed C–C bond cleavage. Chin. J. Chem.. 2011;29(9):1880-1886.
[Google Scholar]

[29] Cain R.B., Freer A.A., Kirby G.W., Rao G.V., . Resolution of (±)-3-methylmuconolactone and the absolute configurations of the naturally occurring 3-and 4-methylmuconolactones: X-ray crystal structures of (S)-1-phenylethylammonium salts and a bromodilactone. J. Chem. Soc., Perkin Trans.. 1989;1(1):202-203.
[Google Scholar]

[30] Capon R.J., MacLeod J.K., . A new sesterterpene tetronic acid from an Australian sponge, Ircinia sp. Aust. J. Chem.. 1987;40(7):1327-1330.
[Google Scholar]

[31] Chapman O.L., Miller M.D., Pitzenberger S.M., . Infrared spectroscopy of matrix-isolated propadienone. J. Am. Chem. Soc.. 1987;109(22):6867-6868.
[Google Scholar]

[32] Chen T., Benmohamed R., Arvanites A.C., Ranaivo H.R., Morimoto R.I., Ferrante R.J., Silverman R.B., . Arylsulfanyl pyrazolones block mutant SOD1-G93A aggregation. Potential application for the treatment of amyotrophic lateral sclerosis. Bioorg. Med. Chem. Lett.. 2011;19(1):613-622.
[Google Scholar]

[33] Cheng C., Jiang B., Tu S., Li G., . [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives. Green Chem.. 2011;13(8):2107-2115.
[Google Scholar]

[34] Cole K.P., Hahn J.M., Hsung R.P., McLaughlin M.J., Wang J.A., . A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(±)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones. Organic Lett.. 2001;4(12):2017-2020.
[Google Scholar]

[35] Colombo F., Cravotto G., Palmisano G., Penoni A., Sisti M., . Three-component indium-mediated domino allylation of 1H-indole-3-carbaldehyde with electron-rich (hetero) arenes: highly efficient access to variously functionalized indolylbutenes. Eur. J. Org. Chem.. 2008;16:2801-2807.
[Google Scholar]

[36] Combs A.P., Crawley M.L., McLaughlin E., Zhu W., . Concise approach to novel isothiazolidinone phosphotyrosine mimetics: microwave-assisted addition of bisulfite to activated olefins. Org. Lett.. 2005;7(22):5067-5069.
[Google Scholar]

[37] Cook G.R., Beholz L.G., Stille J.R., . Construction of hydroxylated alkaloids (+/−)-mannonolactam, (+/−) deoxymannojirimycin, and (+/−)-prosopinine through aza-annulation. J. Org. Chem.. 1994;59(13):3575-3584.
[Google Scholar]

[38] Dal Pozzo A., Dansi A., Neneghini E., . Unsaturated gamma-lactones. Relationship between their structure and antimicrobial activity. Bull. Chim. Farm.. 1974;113(5):280-324.
[Google Scholar]

[39] Darwish O.S., Hahn J.M., Hsung R.P., Liu J., Sydorenko N., Hahn J.M., . Tetronamides as latent acyclic vinylogous amides in formal Aza-[3+3] cycloaddition reactions with α,β-unsaturated iminium salts. An unexpected rearrangement and an approach to synthesis of substituted piperidines. J. Org. Chem.. 2004;69(20):6732-6738.
[Google Scholar]

[40] De Guzman F.S., Schnutz F.J., . Peroxy aliphatic esters from the sponge plakortis lita. J. Nat. Prod.. 1990;53:926-931.
[Google Scholar]

[41] Desbene-Finck S., Giorgi-Renault S., Helissey P., Labruere R., . Efficient syntheses of thiono and dithio analogues of tetronic acid. Synthesis. 2006;24:4163-4166.
[Google Scholar]

[42] Duncanson L.A., . Infra-red spectroscopy and structural chemistry. Part IV. The infra-red spectra of some tetronic acids. J. Chem. Soc. 1953:1207-1211.
[Google Scholar]

[43] Edsall J.T., Sagall E.L., . Raman spectra of l-ascorbic acid, tetronic acid and related compounds. J. Am. Chem. Soc.. 1943;65(7):1312-1316.
[Google Scholar]

[44] Foden F.R., McCormick J., O’Mant D.M., . Vulpinic acids as potential antiinflammatory agents. 1. Vulpinic acids with substituents in the aromatic rings. J. Med. Chem.. 1975;18(2):199-203.
[Google Scholar]

[45] Gan K.H., Jhong C.J., Yang S.C., . Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water. Tetrahedron. 2008;64(7):1204-1212.
[Google Scholar]

[46] Ge P., Kirk K.L., . Synthesis of 2-fluorotetronic acid. J. Fluorine Chem.. 1997;84(1):45-47.
[Google Scholar]

[47] Gelin S., Pallet P., . Tetronic acids and derivatives part VIII (1) o-alkylation of 3-unsubstituted tetronic acids. Syn. Comm.. 1980;10(11):805-811.
[Google Scholar]

[48] Geraghty N.W.A., Kennedy B.D., Murphy P.V., O’Sullivan T.J., . The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: benzofuran formation. J. Chem. Soc., Perkin Trans.. 2000;1(13):2121-2126.
[Google Scholar]

[49] Gérard S., Renzetti A., Lefevre B., Fontana A., de Maria P., Sapi J., . Multicomponent reactions studies: yonemitsu-type trimolecular condensations promoted by Ti (IV) derivatives. Tetrahedron. 2010;66(16):3065-3069.
[Google Scholar]

[50] Ghahremanzadeh R., Naeimi H., Rashid Z., Zarnani A.H., . Synthesis of novel spirooxindoles in water by using MnFe₂O₄ nanoparticles as an efficient magnetically recoverable and reusable catalyst. Appl. Catal.. 2013;467:270-278.
[Google Scholar]

[51] Goddard R., Huang X., Maulide N., . A direct ylide transfer to carbonyl derivatives and heteroaromatic compounds. Angew. Chem. Int. Ed. Engl.. 2010;49(47):8979-8983.
[Google Scholar]

[52] Greenhill J.V., Ramli M., Tomassini T., . Reduction of enaminones in the preparation of 3-aminocyclohexanols; a novel preparation of tetronic acid. J. Chem. Soc. Perkin Trans. 1. 1975;6:588-591.
[Google Scholar]

[53] Greenhill J.V., Tomassini T., . A new and easier route to tetronic acid. Tetrahedron Lett.. 1974;15(31):2683-2684.
[Google Scholar]

[54] Grigg R., Kennewell P., Savic V., . Palladium catalysed cross-coupling of vinyl triflates with 9-alkyl-9-borobicyclo[3,3,1]nonanes. Total synthesis of (−)-isoseiridine. Tetrahedron. 1994;50(18):5489-5494.
[Google Scholar]

[55] Grigg R., Savic V., Thornton-Pett M., . 4-Substituted protoanemonin in intramolecular cycloaddition reactions of non-stabilised azomethine ylides. Tetrahedron. 1997;53(30):10633-10642.
[Google Scholar]

[56] Hamada Y., Shiori T., . New methods and reagents in organic synthesis. 49. A highly efficient stereoselective synthesis of l-daunosamine through direct C-acylation using diphenyl phosphorazidate (DPPA) Tetrahedron Lett.. 1984;25(47):5409-5412.
[Google Scholar]

[57] Han C., Zhang T., Zhang A., Wang D., Shi W., Tao J., . Efficient catalyst-free one-pot three-component synthesis of novel spiro-oxindole derivatives, and their cytotoxic activities. Synthesis. 2014;46(10):1389-1398.
[Google Scholar]

[58] Haque M.A., Nishino H., . Synthesis of peroxylactones using Mn (III)-catalyzed aerobic oxidation. Heterocycles. 2011;83:1783-1805.
[Google Scholar]

[59] Haynes L.J., Kirkien Konasiewicz A., Loudon A.G., Maccoll A., . The fragmentation of organic molecules under electron‐IMPACT—II. The mass spectra of tetronic acid and some of its derivatives. Org. Mass Spectrom.. 1968;1(6):743-759.
[Google Scholar]

[60] Haynes L.J., Plimmer J.R., . Tetronic acids. Quart. Rev.. 1960;14:292-315.
[Google Scholar]

[61] Hoffmann H.M.R., Schmidt B., Wolff S., . Preparation of 5-bromotetronates [4-alkoxy-5-bromo-2 (5H)-furanones] and a new concept for the synthesis of aflatoxins and related structure types. Tributyltin hydride versus palladium-promoted intramolecular hydroarylation. Tetrahedron. 1989;45(19):6113-6126.
[Google Scholar]

[62] Hu Y., Ding Q., Ye S., Peng Y., Wu J., . Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C–OH bond activation. Tetrahedron. 2011;67(38):7258-7262.
[Google Scholar]

[63] Hu Y., Wang J., Lu A., Yang C., . Synthesis, characterization, antifungal evaluation and 3D-QSAR study of phenylhydrazine substituted tetronic acid derivatives. Bioorg. Med. Chem. Lett.. 2014;24(16):3772-3776.
[Google Scholar]

[64] Ibi A., Taniguchi E., Maekawa K., . Syntheses and biological activities of tetramic acid and tetronic acid derivatives [growth regulators] Agric. Biol. Chem.. 1979;43:1641-1646.
[Google Scholar]

[65] Iida A., Kano M., Kubota Y., Koga K., Tomioka K., . Targeting DNA topoisomerase II with podophyllotoxin aza-analogue. Bioorg. Med. Chem. Lett.. 1997;7(20):2565-2566.
[Google Scholar]

[66] Iwata S., Ishiguro Y., Utsugi M., Mitsuhashi K., Tanaka K., . 3,3,3-Trifluoro-1-nitropropene as a novel trifluoromethyl-containing building block. Bull. Chem. Soc. Jpn.. 1993;66(8):2432-2435.
[Google Scholar]

[67] Jas G., . A simple resolution of 4-bromo-2-(tert-butyldimethylsiloxy)furan from tetrahydro-2,4-dioxofuran. Synthesis. 1991;11:965-966.
[Google Scholar]

[68] Jeedimalla N., Johns J., Roche S.P., . Mechanistic investigation and implications of a sacrificial aniline for the tandem cascade synthesis of 4-aza-podophyllotoxin analogues. Tetrahedron Lett.. 2013;54(44):5845-5848.
[Google Scholar]

[69] Jurd L., . New anti-tumor agents. 3. Phenolic benzopyran lactone and amine derivatives. J. Heterocyclic Chem.. 1997;34(2):601-604.
[Google Scholar]

[70] Jurd L., . New anti-tumor agents heterocyclic benzodioxole lactones. J. Heterocyclic Chem.. 1996;33:1227-1232.
[Google Scholar]

[71] Kamal A., Reddy T.S., Polepalli S., Paidakula S., Srinivasulu V., Reddy V.G., Shankaraiah N., . Synthesis and biological evaluation of 4-aza-2,3-dihydropyridophenanthrolines as tubulin polymerization inhibitors. Bioorg. Med. Chem. Lett.. 2014;24(15):3356-3360.
[Google Scholar]

[72] Kamal A., Tamboli J.R., Nayak V.L., Adil S.F., Vishnuvardhan M.V.P.S., Ramakrishna S., . Synthesis of a terphenyl substituted 4-aza-2,3-didehydropodophyllotoxin analogues as inhibitors of tubulin polymerization and apoptosis inducers. Bioorg. Med. Chem.. 2014;22(9):2714-2723.
[Google Scholar]

[73] Kametani T., Katoh T., Tsubuki M., Honda T., . Stereoselective synthesis of 26,27-bisnorbrassinolide. Chem. Pharm. Bull.. 1987;35(6):2334-2338.
[Google Scholar]

[74] Kametani T., Katoh T., Tsubuki M., Honda T., . One-step stereochemical determination of four contiguous acyclic chiral centers on a steroidal side chain: a novel synthesis of brassinolide. J. Am. Chem. Soc.. 1986;108(22):7055-7060.
[Google Scholar]

[75] Kaoua R., Kaoua R., Le Gal Y., Lorcy D., Roisnel T., Kaoua R., Nedjar-Kolli B., . Electroactive 1,5-benzodiazepines bearing either a tetrathiafulvalene or a ferrocene moiety. Tetrahedron. 2013;69(23):4636-4640.
[Google Scholar]

[76] Kotha S., Deb A.C., . Design and synthesis of spiro-heterocycles by ring-closing metathesis. Indian J. Chem.. 2008;47(7):1120-1134.
[Google Scholar]

[77] Kotha S., Deb A.C., Kumar R.V., . Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction. Bioorg. Med. Chem. Lett.. 2005;15(4):1039-1043.
[Google Scholar]

[78] Kozlov N.G., Bondarev S.L., Kadutskii A.P., Basalaeva L.I., Pashkovskii F.S., . Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained. Russ. J. Org. Chem.. 2008;44(7):1031-1037.
[Google Scholar]

[79] Ley S.V., Trudell M.L., Wadsworth D.J., . The total synthesis of agglomerin A and (±)-carolinic acid. A general method for the preparation of 3-acyl tetronic acids via direct acylation of O-methyl 3-stannyl tetronates. Tetrahedron. 1991;47(38):8285-8296.
[Google Scholar]

[80] Ley S.V., Wadsworth D.J., . Preparation of O-methyl 3-acyl tetronic acids by the direct acylation of stannyl tetronates. Tetrahedron Lett.. 1989;30:1001-1004.
[Google Scholar]

[81] Luk K., Readshaw S.A., . Structural studies of MM46115, a novel tetronic acid containing macrolide with antiviral and antibacterial activity isolated from Actinomadura pelletieri. J. Chem. Soc., Perkin Trans.. 1991;1(7):1641-1644.
[Google Scholar]

[82] Madec D., Mingoia F., Prestat G., Poli G., . N-substituted tetronamides as ambident nucleophilic building blocks for the synthesis of new 4-aza-2,3-didehydropodophyllotoxins. Synlett. 2008;10:1475-1478.
[Google Scholar]

[83] Martoglio P.A., Katon J.E., . The vibrational assignment of tetronic acid. J. Mol. Struct.. 1993;296(1):35-51.
[Google Scholar]

[84] Matsumoto M., Kawamura Y., Yoshimura Y., Terui Y., Nakai H., Yoshida H.I., Shoji I., . Isolation, characterization and structures of PA-46101 A and B. J. Antibiot.. 1990;43(7):739-747.
[Google Scholar]

[85] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . A facile synthesis, tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes. Color. Technol.. 2013;129(6):418-424.
[Google Scholar]

[86] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . A worthy insight into the dyeing applications of azo pyrazolyl dyes. Int. J. Modern Org. Chem.. 2012;1(3):165-192.
[Google Scholar]

[87] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Pyrazol-5-ones: tautomerism, synthesis and reactions. Int. J. Modern Org. Chem.. 2012;1(1):19-54.
[Google Scholar]

[88] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, structure investigation and dyeing assessment of novel bisazo disperse dyes derived from 3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones for dyeing polyester fabrics. J. Korean Chem. Soc.. 2012;56(3):348-356.
[Google Scholar]

[89] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, structure elucidation and application of some new azo disperse dyes derived from 4-hydroxycoumarin for dyeing polyester fabrics. Am. J. Chem.. 2012;2(6):347-354.
[Google Scholar]

[90] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, tautomeric structure, dyeing characteristics, and antimicrobial activity of novel 4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones. J. Korean Chem. Soc.. 2012;56(1):82-91.
[Google Scholar]

[91] Metwally M.A., Bondock S., El-Desouky E.I., Abdou M.M., . Synthesis, spectroscopic studies and technical evaluation of novel disazo disperse dyes derived from 3-(2-hydroxyphenyl)-2-pyrazolin-5-ones for dyeing polyester fabrics. Am. J. Chem.. 2013;3(4):59-67.
[Google Scholar]

[92] Miller M., Hegedus L.S., . Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita. J. Org. Chem.. 1993;58(24):6779-6785.
[Google Scholar]

[93] Miller T.A., Vachaspati P.R., Labroli M.A., Thompson C.D., Bulman A.L., Macdonald T.L., . The synthesis and evaluation of benzannelated-azatoxins: the benzazatoxins. Bioorg. Med. Chem. Lett.. 1998;8(9):1065-1070.
[Google Scholar]

[94] Momose T., Toyooka N., Nishi T., Takeuchi Y., . (3H)- and 2(5H)-furanones. III. An efficient synthesis and the eschenmoser-mannich reaction of unsubstituted 4-amino-2(5H)-furanone. Heterocycles. 1988;27(8):1907-1924.
[Google Scholar]

[95] Moreno-Mañas M., Prat M., Ribas J., Virgili A., . Palladium catalyzed allylic C-alkylation of highly acidic and enolic heterocyclic substrates: tetronic acid and triacetic acid lactone. Tetrahedron Lett.. 1988;29(5):581-584.
[Google Scholar]

[96] Murray E.J., Crowley R.C., Truman A., Clarke S.R., Cottam J.A., Jadhav G.P., Steele V.R., O’Shea P., Lindholm C., Cockayne A., Chhabra S.R., Chan W.C., Williams P., . Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors. J. Med. Chem.. 2014;57(6):2813-2819.
[Google Scholar]

[97] Nomura K., Hori K., Arai M., Yoshii E., . An efficient method for 3 (C)-acylation of tetronic acids. Chem. Pharm. Bull.. 1986;34(12):5188-5190.
[Google Scholar]

[98] Otto W., . Nitrogen-containing derivatives of tetronic acid. Arch. Pharm.. 1987;320(8):749-755.
[Google Scholar]

[99] Pashkovskii F.S., Katok Y.M., Khlebnikova T.S., Koroleva E.V., Lakhvich F.A., . Heterocyclic analogs of prostaglandins: I. Synthesis of 3-alkyl (aralkyl)-2,5-dihydrofuran-2-ones as synthons for 11-deoxy-10-oxaprostanoids. Russ. J. Org. Chem.. 2003;39(7):998-1009.
[Google Scholar]

[100] Pashkovskii F.S., Shchukina E.M., Gribovskii M.G., Lakhvich F.A., . Heterocyclic analogs of prostaglandines: IV. Synthesis of 3,7-interphenylene 3,10 (11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes. Russ. J. Org. Chem.. 2008;44(5):657-670.
[Google Scholar]

[101] Paulvannan K., Stille J.R., . Heterocycle formation through aza-annulation: stereochemically controlled syntheses of (+/−)-5-epitashiromine and (+/−)-tashiromine. J. Org. Chem.. 1994;59(7):1613-1620.
[Google Scholar]

[102] Pollet P.L., Perzanowski H.P., Gelin S., . Tautomerism in 3-nitrotetronic acids. Spectrochim. Acta Mol. Biomol. Spectrosc.. 1984;40(11):1007-1009.
[Google Scholar]

[103] Pollet P., Gelin S., . Tetronic acids and derivatives-IV: synthesis and lactonization of-γ-acetoxy β-ketoesters. Tetrahedron. 1978;34(10):1453-1455.
[Google Scholar]

[104] Prat M., Moreno-Mañas M., Ribas J., . Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds. Tetrahedron. 1988;44(23):7205-7212.
[Google Scholar]

[105] Pugh G., Zhang W., Zhang W., . Free radical reactions for heterocycle synthesis. Part 7: 2-bromobenzoic acids as building blocks in the construction of spirobenzolactones and spirobenzolactams. Tetrahedron. 2003;59(24):4237-4247.
[Google Scholar]

[106] Ramachary D.B., Kishor M., . Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1, 5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions. Org. Biomol. Chem.. 2010;8(12):2859-2867.
[Google Scholar]

[107] Rehse K., Emisch U., . Tetronsäuren mit direkten antikoagulanten Wirkungen. Arch. Pharm.. 1983;316(2):115-120.
[Google Scholar]

[108] Rehse K., Rothe M., . Untersuchungen Zur Eiweißbindung Von Arzneistoffen Durch Kontinuierliche Ultrafiltration. 4. Mitt. Arch. Pharm.. 1982;315(3):259-262.
[Google Scholar]

[109] Rehse K., Wagenknecht J., Rietbrock N., . Anticoagulant activity of 3,5-disubstituted tetronic acids. Arch. Pharm.. 1978;311(12):986.
[Google Scholar]

[110] Ribbons D.W., Sutherland A.G., . (+)-Muconolactone from arene biotransformation in Pseudomonas putida: production, absolute configuration and enantiomeric purity. Tetrahedron. 1994;50(11):3587-3594.
[Google Scholar]

[111] Roggo B.E., Petersen F., Delmendo R., Jenny H.B., Peter H.H., Roesel J., . 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin new inhibitors of HIV-1 protease. I. Fermentation isolation and biological activity. J. Antibiot.. 1994;47(2):136-142.
[Google Scholar]

[112] Rouleau J., Korovitch A., Lion C., Hémadi M., Ha-Duong N.T., El Hage Chahine J.M., Le Gall T., . Synthesis and evaluation of 3-acyltetronic acid-containing metal complexing agents. Tetrahedron. 2013;69(51):10842-10848.
[Google Scholar]

[113] Rupprecht J.K., Hui Y.H., McLaughlin J.L., . Annonaceous acetogenins: a review. J. Nat. Prod.. 1990;53(2):237-278.
[Google Scholar]

[114] Sato M., Sakaki J.I., Takayama K., Kobayashi S., Suzuki M., Kaneko C., . A novel synthetic method for tetronic acids from 1,3-dioxin-4-ones via intra-or intermolecular ketene trapping. Chem. Pharm. Bull.. 1990;38(1):94-98.
[Google Scholar]

[115] Savina S.A., Lyubchanskaya V.M., Alekseeva L.M., Shashkov A.S., Granik V.G., . Synthesis of novel furoquinolines and furobenzodiazepines from tetronic acid. Russ. Chem. Bull.. 2007;56(11):2298-2304.
[Google Scholar]

[116] Schiehser G.A., White J.D., Matsumoto G., Pezzanite J.O., Clardy J., . The structure of leptosphaerin. Tetrahedron Lett.. 1986;27(46):5587-5590.
[Google Scholar]

[117] Schmidt D.G., Seemuth P.D., Zimmer H., . Substituted. gamma.-butyrolactones. Part 31.2,4(3H,5H)-furandione: heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones. J. Org. Chem.. 1983;48(11):1914-1916.
[Google Scholar]

[118] Schmidt D.G., Zimmer H.A., . Convenient synthesis of 2,4(3H, 5H)-furandione (β-tetronic acid) Synth. Commun.. 1981;11(5):385-390.
[Google Scholar]

[119] Shaabani A., Sarvary A., Keshipour S., Rezayan A.H., Ghadari R., . Unexpected Knoevenagel self-condensation reaction of tetronic acid: synthesis of a new class of organic heterocyclic salts. Tetrahedron. 2010;66(10):1911-1914.
[Google Scholar]

[120] Shue Y.J., Yang S.C., . Activator-free and one-pot C-allylation by simple palladium catalyst in water. Tetrahedron Lett.. 2012;53(11):1380-1384.
[Google Scholar]

[121] Stachel H., Poschenrieder H., Redlin J., Schachtner J., Zeitler K., . Reductones of tetronic, thiotetronic and tetramic acids, II. Reductones by rhodium-catalyzed decomposition of diazo compounds. Liebigs Ann. Chem.. 1994;2:129-132.
[Google Scholar]

[122] Sun X., Wu J., Zhang L., . Efficient route to 4-substituted-2 (5H)-furanones, 2 (1H)-quinolones, and pyrones by nickel-catalyzed cross-coupling of arenesulfonates with organozinc reagents. Chem. Lett.. 2005;34(6):796-797.
[Google Scholar]

[123] Svendsen A., Boll P.M., . Naturally occuring lactones and lactames-V: halogenated β-keto esters as starting materials for the synthesis of tetronic acids. Tetrahedron. 1973;29(24):4251-4258.
[Google Scholar]

[124] Tanaka K., Matsuo K., Nakanishi A., Jo M., Shiota H., Yamaguchi M., Kawaguchi K., . Syntheses and antimicrobial activities of five-membered heterocycles having a phenylazo substituent. Chem. Pharm. Bull.. 1984;32(8):3291-3298.
[Google Scholar]

[125] Tejedor D., García-Tellado F., . Synthesis and chemistry of tetronic acids. Org. Prep. Proc. Int.. 2004;36(1):33-59.
[Google Scholar]

[126] Vanwagenen B.C., Cardellina J.H. II, . Native american food and medicinal plants 7: antimicrobial tetronic acid from lomatium dissectum. Tetrahedron. 1986;42(4):1117-1122.
[Google Scholar]

[127] Vieweg L., Reichau S., Schobert R., Leadlay P.F., Süssmuth R.D., . Recent advances in the field of bioactive tetronates. Nat. Prod. Rep.. 2014;31(11):1554-1584.
[Google Scholar]

[128] Villemin D., Labiad B., . Clay catalysis: dry condensation of tetronic acid with aldehydes under microwave irradiation. Synthesis of 3-(arylmethylene)-2,4-(3H, 5H) furandiones. Synth. Commun.. 1990;20(20):3207-3212.
[Google Scholar]

[129] Vishwakarma R.A., Kapil R.S., Popli S.P., . Studies in medicinal-plants. New lactones from hypericum-mysorense. Indian J. Chem.. 1987;26(5):486-487.
[Google Scholar]

[130] Wang L., Wu J., Zhu Q., Fathi R., Yang Z., Yang Z., . Palladium-catalyzed cross-coupling reactions of 4-tosyl-2 (5H)-furanone with boronic acids: a facile and efficient route to generate 4-substituted 2 (5H)-furanones. J. Org. Chem.. 2003;68(2):670-673.
[Google Scholar]

[131] Wegnel A.S., Reffstrup T., Boll P.M., . Regiospecific alkylation of tetronic acids: formation of 4-alkoxy-5H-furan-2-ones and 2-alkoxy-5H-furan-4-ones. Terrahedron. 1979;35(18):2181-2185.
[Google Scholar]

[132] Witiak D.T., Kokrady S.S., Patel S.T., Akbar H., Feller D.R., Newman H.A., . Hypocholesterolemic and antiaggregatory properties of 2-hydroxytetronic acid redox analogs and their relationship to clofibric acid. J. Med. Chem.. 1982;25(1):90-93.
[Google Scholar]

[133] Wolffe, L., Schwabe, C., 1896. Tetronic acid. Liebigs. J. Ann. Chem. 292, 231; Chem. Abstr., 70, I, 522–524.

[134] Xie Z.B., Wang N., Wu M.Y., He T., Le Z.G., Yu X.Q., . Catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to nitroalkenes by a grinding method. Beilstein J. Org. Chem.. 2012;8(1):534-538.
[Google Scholar]

[135] Xin Z., Zheng G.Z., Stewart A.O., . 2-Siloxy-4-furanyl anion: remarkable solvent effect on its nucleophilicity. Synlett. 2000;9:1324-1326.
[Google Scholar]

[136] Zhang C.L., Chatterjee S.S., Stein U., Heinemann U., . Comparison of the effects of losigamone and its isomers on maximal electroshock induced convulsions in mice and on three different patterns of low magnesium induced epileptiform activity in slices of the rat temporal cortex. Naunyn-Schmideberg’s Arch. Pharmacol.. 1992;345(1):85-92.
[Google Scholar]

[137] Zhang W., . Free radical reactions for heterocycle synthesis. Part 3: formation of novel spirodilactones, spirolactone-lactams, andes spirolactone-thiolactones. Tetrahedron Lett.. 2000;41(15):2523-2527.
[Google Scholar]

[138] Zimmer H., Amer A., Pham C.V., Schmidt D.G., Zimmer H., Amer A., Van P.C., Schmidt D.G., . On the synthesis of 4-alkoxy-2 (5H)-furanones. J. Org. Chem.. 1988;53(14):3368-3370.
[Google Scholar]

[139] Zimmer H., Hillstrom W.W., Schmidt J.C., Seemuth P.D., Vogeli R., . Substituted. gamma.-lactones. 28. 3-(phenylmethylene)-2,4-(3H, 5H) furandiones. J. Org. Chem.. 1978;43(8):1541-1544.
[Google Scholar]

[140] Zografos A.L., Georgiadis D., . Synthetic strategies towards naturally occurring tetronic acids. Synthesis. 2006;19:3157-3188.
[Google Scholar]

Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions

Abstract

Keywords

Tetronic acid

Synthetic routes

Chemical reactivity

Tautomeric structure

Reactions

1 Introduction

2 Tautomeric structure(s)

3 Synthesis

3.1 Using 1, 3-dioxin-4-one

3.2 Using lactonization of γ-acetoxy-β-keto esters

3.3 Debromination of α-bromotetronic

4 Chemical reactions

4.1 Reactions involving carbon–carbon bond formation

4.1.1 C–C bond formation reactions

4.1.1.1 C3-alkylation

4.1.1.2 C3-allylation reaction

4.1.1.3 C3-benzylation

4.1.1.4 Arylation

4.1.1.5 Olefination

4.1.1.6 Allylindation

4.1.1.7 Acetylation reaction

4.2 Reactions involving carbon–heteroatom bond formation

4.2.1 C–N bond formation

4.2.1.1 Coupling reactions

4.2.1.2 Nitration reaction

4.2.1.3 Amination reaction

4.2.1.4 Diazotization reactions

4.2.2 C–S bond formation

4.2.2.1 Sulfonation reaction

4.2.2.2 Thionation reaction

4.2.3 C–O bond formation

4.2.3.1 Esterification

4.2.3.2 O-alkylation reaction

4.2.3.3 Sulfonates ether formation

4.2.3.4 Phosphorylation reaction

4.2.4 Carbon–halogen bond formation

4.2.4.1 Bromination

5 Conclusion

References

Suggested read for related articles:

4.1.1.1 C₃-alkylation

4.1.1.2 C₃-allylation reaction

4.1.1.3 C₃-benzylation