Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity

Moaz M. Abdou; Rasha A. El-Saeed; Samir Bondock

doi:10.1016/j.arabjc.2015.06.029

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REVIEW

12 (

); 974-1003

doi:

10.1016/j.arabjc.2015.06.029

Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity

Moaz M. Abdou^{^a,^d,⁎}, Rasha A. El-Saeed^{^b}, 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: 2014-12-5, Accepted: 2015-6-26, Published: 2015-11-01

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

Abstract

The present paper aims to review the synthetic applicability of 4-hydroxycoumarin in heterocyclic synthesis during the period from 1996 up to now. This compound can be used as building blocks for five, six, and seven-membered heterocycles as well as fused rings.

Keywords

4-Hydroxycoumarin

Annelated heterocycles

Multicomponent reactions

Green chemistry

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1 Introduction

4-Hydroxycoumarin is a well-known versatile synthon and important reagents in the realm of heterocyclic synthesis (Abdolmohammadi, 2014; Abdou et al., 2013; Aggarwal et al., 2013; Ahadi et al., 2014; Altieri et al., 2010; Azizi et al., 2014; Bakthadoss and Sivakumar, 2014; Chen et al., 2013; Darehkordi et al., 2014; Davarpanah and Kiasat, 2014; Eskandari et al., 2013; Ghosh and Khan, 2014; Golzar et al., 2013; Gu et al., 2009; Hossain et al., 2013; Hossaini et al., 2013; Jashari et al., 2014; Jin et al., 2013; Jung and Park, 2009; Lee et al., 2012; Mei et al., 2013; Metwally et al., 2013, 2012a, 2012b, 2012c, 2012d; Mungra et al., 2011; Nair et al., 2014; Nishino et al., 2014; Pal et al., 2013; Ponpandian and Muthusubramanian, 2014; Rad-Moghadam et al., 2014; Rajawat et al., 2014; Saha, 2013; Sato et al., 2013; Siddiqui and Khan, 2013, 2014; Xiao et al., 2014; Zhao and Du, 2014; Ziarani and Hajiabbasi, 2013 ). It is of particular interest as a very promising reagent for cascade heterocyclization, which will undoubtedly become one of the main approaches to the targeted synthesis of heterocycles in the near future, in the rapidly-rising field of combinatorial chemistry.

In a continuation of our research program aiming at the utilization of cyclic 1,3-diketone compounds as scaffolds for heterocycle molecular diversity (Abdou, 2017a, 2017b, 2017, 2018, 2017, 2013b, 2013c; Abdou et al., 2013, 2012 ), the first part of this review article (Abdou, 2019) is dealt with most recent advances in 4-hydroxycoumarin chemistry made since 1996 up to date and concentrates on synthesis, chemical reactivity and reactions of 4-hydroxycoumarin. The second part intends to illustrate the research efforts that occurred in the application of 4-hydroxycoumarin in heterocyclic synthesis covering the same period of time. The presence of reactive centers in this compound provides ample opportunities to synthesize a great variety of novel compounds under relatively mild conditions and using simple laboratory equipments. Thus, the two parts are complementary and display current trends in 4-hydroxycoumarin chemistry.

In this literature survey, the reactions involving 4-hydroxycoumarin occur with high regioselectivity and its course can easily be controlled by changing reaction conditions and varying substituents in the molecules of initial compounds. The heterocyclic compounds are obtained in a single step with high yield and they are reported in order of the increase of (i) the number of rings, (ii) the size of such rings and (iii) the number of heteroatoms present. The sequence of heteroatoms followed is: nitrogen, oxygen and sulfur. The site of fusion in fused heterocycles is indicated by the numbers and letters and the numbering of the heterocyclic ring systems is that reported by chemical abstracts.

2 Synthesis of monocyclic heterocyclic compounds

2.1

2.1 Synthesis of five-membered systems with two heteroatoms

2.1.1

2.1.1 Pyrazolin-5-ones

Froggett et al. (1997) described the reaction of 4-hydroxycoumarin 1 with a 1.5 equimolar excess of 4-chlorophenylhydrazine 2 in toluene under reflux, with azeotropic removal of water, furnished the 1-(4-chlorophenyl)-3-(2-hydroxy-phenyl)-2-pyrazolin-5-one 3 (Scheme 1).

The solvent-free reactions of substituted hydrazine hydrochlorides 4 with 1 in the presence of triethylamine were carried out by heating in the absence of solvent (90 min, 90–100 °C). In all cases, 1-aryl-3-(2-hydroxyphenyl)pyrazol-5-ones 6a-c were formed along with the corresponding 4-(arylhydrazino) coumarins 5a-c (Strakova et al., 2009) (Scheme 2).

3-(2-Hydroxyphenyl)-1-methyl-1H-pyrazol-5-one 8 was obtained from the reaction of 1 with methylhydrazine 7 in ethanol. The reaction mixture was refluxed under N₂ flow (Zhao et al., 2010) (Scheme 3).

2.1.2

2.1.2 Imidazol-2(3H)-ones

The one-pot condensation of 1 with arylglyoxals 9 and ureas 10 in refluxing ethanol in the presence of a catalytic amount of acetic acid gave a colorless crystalline products that were identified as 4-aryl-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1H-imidazol-2(3H)-ones 11 (Kolos et al., 2009) (Scheme 4).

2.1.3

2.1.3 1,2-Benzisoxazoles

Reaction of 1 with hydroxylamine hydrochloride in refluxing methanol represents one of the most successful strategies to attain 1,2-benzisoxazole-3-acetic acid 12, which has been widely exploited because of their known important biological activities and application in different therapies (Lamani et al., 2009) (Scheme 5).

2.2

2.2 Synthesis of five-membered ring systems with more than two heteroatoms

2.2.1

2.2.1 Dithiazoles

The reaction of 1 with 4,5-dichloro-5H-1,2,3-dithiazolium chloride 13 in the presence of pyridine in dichloromethane at room temperature gave the corresponding 5-alkylidene-5H-4-chloro-l,2,3-dithiazoles 14 as a single stereoisomer in 87% yield (Jeon and Kim, 1999) (Scheme 6).

2.3

2.3 Synthesis of six-membered heterocycles containing one heteroatom

2.3.1

2.3.1 Quinoline

In 2010, a fast and solvent-free method was described for the synthesis of substituted quinoline derivatives via Friendländer synthesis is promoted, either under conventional heating or under MW irradiation, catalyzed by a derivatized silica bearing alkylsulfonic acid groups. The reaction of 1 with 2-aminobenzophenone 15 afforded 7-phenyl-6H-chromeno[4,3-b]quinolin-6-one 16 and 2-(4-phenylquinolin-2-yl)phenol 17. The addition of activated molecular–sieve powder to the reacting mixture increased the yield of 16 (40%) while dramatically reducing the yield of 17 (11%), o-hydroxy acetophenone 18 was the main product (about 50%) generated by the partial degradation of excess 4-hydroxycoumarin (Garella et al., 2010) (Scheme 7).

2.4

2.4 Synthesis of seven-membered heterocycles containing two heteroatoms

2.4.1

2.4.1 1,4-Diazepines

It was reported that the condensation of 1 with o-phenylenediamine 19 in refluxing toluene (Hamdi et al., 2006) or under MW irradiation (Kidwai et al., 2005) afforded 4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzo diazepin-2-one (Scheme 8).

3 Synthesis of fused heterocyclic compounds

3.1

3.1 [5-6] Ring system

3.1.1

3.1.1 Pyrano[4,3-d]oxazol-4-ones

Ray and Paul (2004) published the one-pot synthesis of benzo[1]pyrano[4,3-d]oxazol-4-one 22 consisting of the condensation of 1 with formamide 21 under reflux (Scheme 9).

3.1.2

3.1.2 Oxathiolo[5,4-c]-2H-chromen-4-ones

Reaction of 3-(chlorothio)-3-fluoro-2-(trifluoromethyl)-2-propenoic acid methyl ester 23 with 1 leads to sulfenylation accompanied by cyclization giving rise to fused 2-(2,2,2-trifluoro-1-methoxycarbonylethylidene)-oxathiolo[4,5-c]-2H-chromen-4-one 24 (Kovregin et al., 2001) (Scheme 10).

3.1.3

3.1.3 Dihydrofuran and furocoumarins

Furocoumarins are an important class of heterocyclic compounds possessing anticoagulant, insecticide, anthelminthic, hypnotic, antifungal, and HIV protease inhibition activities (Baichurin et al., 2013; Karami et al., 2013; Khan et al., 2013 ).

3.1.3.1

3.1.3.1 Oxidative cycloaddition reaction mediated by metal salts

The oxidative addition reaction of carbon-centered radicals to alkenes mediated by metal salts Ag (I), Ce (IV), Yb (III), Ru (II), and Mg(II) has received considerable attention over the last decade in organic synthesis for construction of carbon–carbon bonds.

3.1.3.1.1

3.1.3.1.1 Using Ag (I)

Lee and Kim (1997) have reported a facile and simple method for the synthesis of dihydrofurans, by the addition of silver (I)/Celite to the mixture of 1 and with ethyl vinyl ether 25 in acetonitrile under reflux (Scheme 11).

In a similar manner, medium- and large-sized ring substituted furans 28 could be also achieved via cycloaddition of 1 with a variety of vinyl sulfides 27 in refluxing acetonitrile (Lee and Kim, 1997) (Scheme 12).

3.1.3.1.2

3.1.3.1.2 Using Ce(IV)

An efficient method for one-step synthesis of substituted 2-arylfurans has been developed by ceric (IV) ammonium nitrate (CAN) mediated oxidative cycloaddition of 1 with phenylacetylene 29 at 0 °C in acetonitrile giving linear and angular furocoumarin derivatives 30 and 31 as a mixture of regioisomers in good yields (Lee et al., 1998) (Scheme 13).

Lee et al. (2000) has also found that CAN(IV) was the much superior reagent for this oxidative cycloaddition than Mn(OAc)₃.2H₂O and Ag₂CO₃/Celite. The reaction was typically carried out at 80 °C starting from 1 with methyl methacrylate 32 in the presence of CAN and excess amounts of sodium bicarbonate in acetonitrile giving the sole biologically interesting dihydrofurocoumarin 33 in 35% yield (Scheme 14).

Appendino et al. (1998) showed that treatment of 1 with 3-buten-2-ol and cerium (IV) ammonium nitrate (CAN) in acetonitrile at room temperature give a mixture of diastereomers 35 and 36 (Scheme 15). No substantial improvement of the ratio between angular and linear adducts could be achieved by changing solvent or metal oxidant and varying the temperature (Scheme 15).

It was also reported that the reaction of 1 with a range of alkenes in acetonitrile containing cerium (IV) ammonium nitrate (CAN) afforded the corresponding furo[3,2-clpyranones 38 and furo[2,3-b]pyranone derivatives 39. It should be noted that the reactions of 1 with vinyl benzoate and methylstyrene produced exclusively the furo[3,2-c]benzopyranone derivatives, as the sole isolated product; no more than a trace amount of the corresponding furo[2,3-b]benzopyranone derivatives was obtained in each of these reactions, while formation of both the furopyranone derivatives was observed using other alkenes (Kobayashi et al., 1999) (Scheme 16).

There has been a considerable interest in the use of CAN oxidation reactions in ionic liquids. Hence, reaction of 1 with methylstyrene 40 and CAN in 1-n-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF₄]-dichloromethane(1:9), gave tricycle 41 in 70% yield after 3 h. The CAN reaction in [bmim][BF₄]-dichloromethane (40 °C) is therefore more efficient and/or faster than reactions (at r.t. or at 40 °C) in acetonitrile. One further and important advantage to the use of [bmim][BF₄] is that on workup, the cerium byproducts form a precipitate at the end of the reaction (Bar et al., 2003) (Scheme 17).

3.1.3.1.3

3.1.3.1.3 Ruthenium(II)

Cadierno et al. (2008) developed a simple strategy for the synthesis of multi-substituted furocoumarins by using a catalytic system consisting of the 16-electron allyl-ruthenium(II) complex [Ru(η3-2-C₃H₄Me)(CO)(dppf)][SbF₆](dppf = 1,1′-bis(diphenylphosphino)ferrocene) and trifluoro acetic acid (TFA) has been used to promote the coupling between secondary propargylic alcohol 42 and 1 to give 3-(4-methoxyphenyl)-2-methyl-furo[3,2-c]chromen-4-one 43 (Scheme 18).

3.1.3.1.4

3.1.3.1.4 Manganese(III) acetate

Yilmaz et al. (2008) have obtained 2,3-dihydro-4H-furo[3,2-c]chromen-4-ones 45 from the radical cyclization of 1 mediated by manganese(III) acetate with electron rich alkenes 44 in 36–86% yields (Scheme 19).

3.1.3.1.5

3.1.3.1.5 Multicopper oxidases (Laccases)

Laccase (Agaricus bisporus)-catalyzed domino reaction of 1 with catechols 46 using atmospheric oxygen as the oxidant delivers for the synthesis of 10-substituted 8,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-ones 47 as single regioisomers with yields of 61–99% (Leutbecher et al., 2011, 2005) (Scheme 20). Some of these compounds have been made accessible by crude peroxidase from onion solid waste (Angeleska et al., 2013).

3.1.3.2

3.1.3.2 [4+1] Cycloaddition reaction followed by a [1,3]-H shift

A [1+4] approach was developed by Majumdar et al. to prepare 3-hydroxy-2,3-dihydrofuro[3,2-c][1]benzopyran-4-one 49 through the reaction of 1 with chloroacetaldehyde 48 in the presence of aq. potassium carbonate at room temperature for 1.5 h (Majumdar and Bhattacharyya, 1997) (Scheme 21).

In a similar manner, Bondock et al. (2011) reported that antimicrobial active 2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-yl)-4-H-furo[3,2-c]chromen-4-one was obtained via treatment of 2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone 50 with 1 in sodium ethoxide solution (Scheme 22).

2,3-Dihydro-2-hydroxy-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)furo[3,2-c]chromen-4-one 53 could be successfully prepared through the reaction of 1 with a 40% aqueous solution of glyoxal 52 in acetonitrile under reflux (Lamani et al., 2009) (Scheme 23).

Interaction of 1 with bromonitroalkenes 54 in aqueous sodium acetate and tetrabutylammonium bromide (TBAB) gave 2,3-dihydrofuro[3,2-c]chromen-4-ones 55 (Xie et al., 2011) (Scheme 24).

3.1.3.3

3.1.3.3 Multicomponent reactions

3.1.3.3.1

3.1.3.3.1 Using of conventional synthesis

Several reports on the synthesis of furocoumarins via the multicomponent reactions of 1 with various arylaldehydes 56 and isocyanide 57 have been published during the last decade. In most of the cases, the yields of the desired furocoumarins 58 were moderate. Moreover, extended reaction times of up to 24 h under reflux conditions in toxic solvents such as benzene or toluene (Nair et al., 2002; Panja et al., 2012; Zhu et al., 2011 ) were required. These drawbacks restrictedly limit the applications for furocoumarin library construction (Scheme 25).

Consequently, there is need to develop a simple, rapid, eco-friendly and easy experimental and products' isolation procedure for the synthesis of these compounds.

3.1.3.3.2

3.1.3.3.2 Using of microwave irradiation

Microwaves accelerated the synthesis of a range of furo[3,2-c]chromen-4-ones 59 via a three-component reaction of 1, arylaldehyde 56 and cyclohexyl isocyanide 57 (Shaabani and Teimouri, 2003; Wu, 2006). By applying a microwave protocol (DMF, 150 °C, 5 min), reduction in reaction times (24 h → 3–5 min), higher yields and less by-products were observed compared to the conventional synthesis (Scheme 26).

3.1.3.3.3

3.1.3.3.3 Using of water

In fact, choice of solvent is one of the problems to face in order to perform eco-efficient processes. The presence of water was proven to be determinate for the success achieved by Shaabani et al. (2004). Further reasons that make water unique compared to other organic solvents are that it is cheap, not inflammable, and more important, it is not toxic. The environment-friendly one-pot three-component condensation reactions of 1, p-substituted benzaldehyde 56, and alkyl or aryl isocyanides 57 in water afforded furocoumarins 59 in good yields (Shaabani et al., 2004) (Scheme 27).

3.1.3.3.4

3.1.3.3.4 Using of solvent-free synthesis

Adib et al. (2009) have devoted considerable attention to an efficient and direct solvent-free synthesis of bioactive furo[3,2-c]chromenes via a one-pot and solvent-free reaction. Thus a mixture of 1, aldehyde 56, and isocyanide 57 underwent a one-pot addition reaction under an argon atmosphere and solvent-free conditions. The reaction proceeded at 180 °C and was complete within 1.5 h to produce N-alkyl-3-arylfuro[3,2-c]chromenes 59 in 91–95% yields (Scheme 28).

3.1.3.3.5

3.1.3.3.5 Using combination of solvent-free supported reagents and microwave

Shaabani et al. (2005b) have shown the combination of solvent-free supported reagents and microwave in the absence of solid supports and classical heating. One-pot method simply involves microwave irradiation of a mixture of p-substituted benzaldehyde 59 and 1 with isocyanides 60 in the presence of montmorillonite K10 to afford the corresponding products 61. The reaction is completed in all cases within 4–5 min. Also, in this approach the use of large volume of benzene or toluene is avoided, work-up considerably simplified, and safety is increased by reducing the risk of over pressure and explosions (Scheme 29).

3.1.3.4

3.1.3.4 Using of electrochemical routes

One of the most successful strategies for the synthesis of 6H-benzofuro[3,2-c][1]benzopyran-6-one derivatives 61 is electrochemical routes. Nematollahi et al. demonstrated the electrochemical oxidation of catechol (60a), 3-methylcatechol (60b), 3-methoxycatechol (60c), 2,3-dihydroxybenzoic acid (60d) and 3,4-dihydroxybenzoic acid (60f) with 1 as a nucleophile in the presence of potassium ferricyanide as an oxidizing agent in aqueous solution (Nematollahi et al., 2005; Golabi and Nematollahi, 1997a, 1997b ) (Scheme 30).

3.2

3.2 Fused [6-6]ring system

3.2.1

3.2.1 Benzopyrano[2,3-b]pyridine

Bandyopadhyay et al. (2010) reported the one-pot synthesis of the 1-benzopyrano[2,3-b]pyridine moiety 63 via Knoevenagel condensation by heating an equimolar mixture of 1 and 2-(monosubstituted amino)chromone-3-carbaldehyde 62 in boiling ethanol containing a catalytic amount of pyridine (Scheme 31).

Maiti et al. (2010) described the one-pot reaction of 2-(N-cinnamyl-N-aryl)amino-4-oxo-4H-1-benzopyran-3-carbaldehydes 64 with 1 by heating in ethanol in the presence of a catalytic amount of pyridine afforded substituted 11-allyl-6,11-dihydro-6-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-1-benzopyrano[2,3-b]quinolin-5H-5-one 65 (Scheme 32).

3.2.2

3.2.2 Pyrido[3,2-c]coumarins

The work of Pandya et al. (2006) demonstrated that various diarylpyrido[3,2-c]coumarins 67 were synthesized in one step by reacting 1 with α,β-unsaturated ketones 66 in the presence of ammonium acetate and acetic acid (Scheme 33).

3.2.3

3.2.3 Chromeno[3,4-b][4,7]phenanthroline

A short and environmental-friendly synthesis of chromeno[3,4-b][4,7]phenanthroline derivatives 70 was accomplished by three-component reactions involving an aromatic aldehyde 68, 6-aminoquinoline 69 and 1 in water, under microwave irradiation without the use of any catalyst (Zhuang et al., 2008) (Scheme 34).

3.2.4

3.2.4 Chromeno[4,3-b]benzo[f]quinolin-6-one

Chromeno[4,3-b]benzo[f]quinolin-6-one derivatives 72 were obtained in good to high yields via the reaction of N-arylidenenaphthalen-2-amine 71 with 1 in aqueous media catalyzed by triethylbenzyl ammonium chloride (TEBAC) (Wang et al., 2006, 2005) (Scheme 35).

3.2.5

3.2.5 Pyrano benzopyrans

Pyrano[3,2-c]chromen-5-one (pyrano[3,2-c]coumarin) is the core of important natural products and heterocyclic structures. Molecules with such a nucleus exhibit a wide range of biological and pharmacological properties, such as antioxidant, anticancer, anti-inflammatory, antiviral, and antibacterial activities (Ahadi et al., 2013; Banard et al., 2002; Ghandi et al., 2013; Magiatis et al., 1998; Mahdavinia and Peikarporsan, 2013; Mail et al., 2002; Shafiee et al., 2011; Siddiqui, 2014 ). Many naturally occurring compounds with pyrano[3,2-c]coumarin skeletons have been isolated, such as isoethuliacoumarin A, isoethuliacoumarin B, isoethuliacoumarin C, ethuliacoumarin A, ethuliacoumarin B, and pterophyllin. In addition, pyrano[3,2-c]coumarin derivatives are also used as novel photochromers with promising applications in many photonic materials (Huang et al., 2007).

3.2.5.1

3.2.5.1 2H,5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione

Many methods for the synthesis of 2H, 5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione derivatives have been reported successively.

3.2.5.1.1

3.2.5.1.1 Using alkyl-2-substituted-3-dimethyl-aminopropenoates

Jakse et al. (2004) observed that the treatment of ethyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 73 with 1 in acetic acid under reflux afforded 3-(1H-indol-3-yl)-2H,5H-pyrano[3,2-c]chromene-2,5-dione 74 (Scheme 36).

There are several reports in the literatures (Jukic et al., 2001a, 2001b; Sorsak et al., 1998; Toplak et al., 1997 ) about the reaction of alkyl 2-[(2,2-disubstituted) ethenyl]amino-3-(dimethylamino)propenoate 75 with 1 in acetic acid for preparation of corresponding 2H,5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione derivatives 76 (Scheme 37).

In 1999, it has been reported that the preparation of 3-(benzyloxycarbonyl)amino-2H,5H-pyrano[3,2-c]benzopyran-2,5-dione 78 was accomplished by the treatment of methyl-2-(benzyloxy carbonyl)amino-3-dimethylaminopropenoate 77 with 1 under reflux (Toplak et al., 1999) (Scheme 38).

3.2.5.1.2

3.2.5.1.2 Using substituted-tetrahydrofuran-2-one or oxopyrrolidine

A unique one step “ring switching” synthesis of (S)-3-(2,5-dioxo-2H,5H-benzo[b]pyrano[4,3,-b]pyran-3-yl)ester 80 is notable when 79 is reacted with 1 in boiling acetic acid (Mihelic et al., 2001) (Scheme 39).

An elegant, efficient one-pot synthesis of 3-hydroxyethyl-2-pyrano[3,2-c]benzopyran-2,5(6H)-dione 82 was achieved by the condensation of 1 with the sodium salt of α-formyl-γ-butyrolactone 81 in the presence of ammonium acetate (Toche et al., 1999) (Scheme 40).

3.2.5.1.3

3.2.5.1.3 Using Pechmann-Duisberg reaction

The Pechmann-Duisberg reaction was employed by Abd El-Aziz et al. (2007) to synthesis 3-(chloromethyl)-2H-benzo[h]chromen-2-one 84 via condensation of 1 with ethyl 4-chloroacetoacetate 83 in the presence of nitrobenzene and anhydrous aluminum chloride (Scheme 41).

3.2.5.1.4

3.2.5.1.4 Using double catalytic activation conditions

Japanese research group presented an effective enantioselective synthetic method based on a concept of double catalytic activation by the use of catalytic amounts of chiral Lewis acid and amine base, respectively. Thus, under the reaction conditions using 2,2,6,6-tetramethylpiperidine (TMP) and the enantio pure complex catalyst derived from the R,R-DBFOX/Ph ligand and nickel(II) perchlorate hexahydrate, the reaction of 1 with 4-bromo-1-crotonoyl-3,5-dimethylpyrazole 85 in tetrahydrofuran at room temperature in the presence of acetic anhydride (Itoh and Kanemasa, 2003) or the absence of it (Itoh et al., 2005), to give the corresponding enol lactones in a good yield (Scheme 42).

3.2.5.2

3.2.5.2 Synthesis of amino-substituted pyranopyranones

Amino-substituted pyranopyranones are useful intermediates for the synthesis of bioactive natural products and pharmaceutical drugs (Dekamin et al., 2013; Jaggavarapu et al., 2014; Khan et al., 2014, 2011; Mehrabi and Abusaidi, 2010; Niknam and Jamali, 2012; Pansuriya et al., 2009; Prasanna and Raju, 2011; Shaabani et al., 2007; Shaterian and Oveisi, 2011; Tabatabaeian et al., 2012; Wang et al., 2010; Zheng and Li, 2011 ).

3.2.5.2.1

3.2.5.2.1 Two-component condensation

A number of publications have been taken out for Michael reactions 1 with a variety of substituted cinnamonitrile 87 in the presence of bases such as morpholine (Dyachenko and Rusanov, 2006; Kislyi et al., 1999), triethylamine (Mahmoud et al., 2009), sodium methoxide (Nesterov et al., 2005) resulted in the corresponding 2-aminopyrano[3,2-c]chromenes 88 (Scheme 43).

In a similar fashion, it was noted that Michael cycloaddition reaction of 1 with various substituted α-cyanocinnamonitriles 89 in ethanolic piperidine under reflux afforded pyrano[3,2-c]coumarins 90 (Bedair et al., 2000; El-Agrody et al., 2000; Abd El-Wahab et al., 2011 ) (Scheme 44).

Shaabani et al. (2008) described an isocyanide-catalyzed reaction between tetracyanoethylene 91 and 1 to afford 2-amino-5-oxopyrano[3,2-c]chromene-3,4,4(5H)-tricarbonitrile 92 in high yield at room temperature (Scheme 45).

The conversion of substituted cinnamonitriles 93 and 1 into 2-amino-4-aryl-4H,5H-pyrano[3,2-c][1]benzopyran-5-one derivatives 94 can be efficiently performed in water as a solvent using a catalytic amount of triethyl-benzylammonium chloride (TEBA) (Wang et al., 2004) or KF-montmorillonite (Tu et al., 2004) (Scheme 46).

3.2.5.2.2

3.2.5.2.2 Three component condensation

3.2.5.2.2.1. Conventional synthesis. The Knoevenagel cyclocondensation of aliphatic aldehyde 56 with malononitrile 95 and 1 in ethanol at 20 °C in the presence of morpholine yielded the corresponding derivatives of 4-alkyl(cycloalkyl)-2-amino-3-cyano-4H-pyran 96 which are potential biologically active compounds. Their analogs are used in the treatment of cardiovascular diseases and CNS disorders, as well as for the protection of crops from herbicide damage (Dyachenko and Chernega, 2006; Dyachenko, 2005) (Scheme 47).

Klokol et al. (1999) described three component condensation of an aliphatic aldehyde 56 with malononitrile 95 and 1 at 20 °C in ethanol containing an equimolar amount of N-methylmorpholine led to the formation of the corresponding derivatives of 4-alkyl(cycloalkyl)-2-amino-3-cyano-4H-pyrans 96 (Scheme 48).

Shestopalov et al. (2005) noted that reaction of 1 with aromatic aldehyde 56 and malononitrile 95 in boiling ethanol in the presence of triethylamine as a catalyst gave substituted 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromenes 96 in high yields (68–93%) (Scheme 49).

Okamoto et al. (1997, 1996) investigated that a reaction of 1, pyruvaldehyde dimethyl acetal 97 and malononitrile 95 in boiling benzene containing piperidine gave 2-amino-3-cyano-4-dimethoxymethyl-4-methyl-5-oxo-4H,5H-pyrano[3,2-c] chromene 98 in 92% yield (Scheme 50).

The one-pot three-component chemoselective condensation reaction of substituted isocyanides 98 with stoichiometric amount of dialkyl acetylenedicarboxylates 99 in the presence of 1 proceeded spontaneously under different conditions led to a facile synthesis of highly functionalized corresponding dialkyl-2-(alkylamino)-5-oxo-4H,5H-pyrano-[4,3-b] pyran-3,4-dicarboxylates 100, in moderate to good yields (68–97%) (Cravotto et al., 2011; Sarma et al., 2010; Tietze et al., 2001; Yavari et al., 2008 ) (Scheme 51).

3.2.5.2.2.2. Using water. The one-pot, three-component reaction of diversely substituted aromatic aldehydes 56 with malononitrile 95 and 1 in water under reflux in the presence of a catalyst (DBU, ([bmim]OH), TBAB, titanium dioxide, sodium tungstate or spinel zinc ferrite) gave, in all cases, the corresponding dihydropyrano[c]chromenes 102 in good to excellent yields (Das et al., 2014; Gong et al., 2009; Khodabakhshi and Baghernejad, 2014; Khodabakhshi et al., 2014; Khurana et al., 2010; Khurana and Kumar, 2009 ) (Scheme 52). It is worthwhile to note that the reaction is faster with aldehydes having electron-withdrawing groups (such as nitro group and halide) than that with electron-donating groups (such as methoxyl group and hydroxyl group).

Heravi et al. (2008) demonstrated an elegant protocol and eco-friendly route to the synthesis of 2-amino-4-aryl-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitriles 101 via a three component reaction of aryl aldehydes 56, malononitrile 95 and 1 using H₆P₂W₁₈O₆₂ .18H₂O, which proceeds efficiently in aqueous ethanol under heating conditions. Many catalysts (DAHP or (S)-proline (Abdolmohammadi and Balalaie, 2007) or MgO (Seifi and Sheibani, 2008) or FeNi₃–SiO₂ (Nasseri and Sadeghzadeh, 2013)) have also been used as another catalysts for this reaction (Scheme 53). Recently, Yao et al. (2013) found that 2-amino-4-aryl-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitriles 101 could be prepared without catalyst in a mixed solvent of ethanol and water.

3.2.5.2.2.3. Using ionic liquid. 1,1,3,3-N,N,N′,N′-Tetramethylguanidinium trifluoroacetate (TMGT) as an ionic liquid, efficiently promoted one-pot, three-component condensation of aldehydes 56, alkylnitriles 95 and 1 afforded pyran annulated heterocyclic systems 101 (Shaabani et al., 2005a) (Scheme 54).

3.2.5.2.2.4. Microwave irradiation. Kidwai and Saxena (2006) exploited an easier, practically convenient, novel, ecologically safe method for the synthesis of pyrano[3,2-c]benzopyran (R = phenyl, 4-chlorophenyl, 2-furyl, 3-indoly, piperonyl, 2-chloro-3-quinolyl) 101 by three-component reaction of aldehyde 56, malononitrile 95 and 1 in aqueous K₂CO₃ as a green catalyst under microwave heating. The observed yields and enhancement in reaction rates can be attributed to the uniform heating effect of microwave (Scheme 55).

3.2.6

3.2.6 3,4-Dihydro-2H,5H-1-benzopyrano[4,3-b]pyran-5-one

Treatment of 1 with 1-aryl-2-[(dimethylamino)methyl]-2-propen-1-ones 102 in dimethylformamide in the presence of a catalytic amount of dimethylamine under reflux conditions afforded 3-benzoyl-3,4-dihydro-2H,5H-1-benzopyrano[4,3-b]pyran-5-ones 103 (Girreser et al., 1998) (Scheme 56).

Proline-promoted efficient enantioselective synthesis of 4-aryl-3,4-dihydro-2H,5H-pyrano[3,2-c]chromene-2,5-diones 105 from 1, Meldrum’s acid 104, and benzaldehydes 56 (Yavari et al., 2008) (Scheme 57). The functionalized chromenes reported in this work may be considered as potentially useful synthetic intermediates because they possess atoms with different oxidation states.

Khurana and Vij (2011) reported that the reaction of 5-arylidene Meldrum’s acids 106 with 1 in the presence PEG-stabilized Ni nanoparticles underwent rapid and tandem enol lactonization involving Michael addition to give 4-aryl-3,4-dihydropyrano[3,2-c]chromene-2,5-diones 107 (Scheme 58).

Three-component cyclocondensation of 1, aldehydes 56, and cyclic 1,3-dicarbonyl compounds 108 were prompted by ionic liquids 1,3-dimethyl-2-oxo-1,3-bis(4-sulfobutyl)imidazolidine-1,3-diium hydrogen sulfate ([DMDBSI].2HSO₄) in water to provide a novel series of 10,11-dihydro-chromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives 109 (Chen et al., 2011) (Scheme 59). Also, this reaction can be achieved using a catalytic amount of heteropolyacids or molecular iodine (Motamedi et al., 2012; Sun et al., 2012).

Cravotto et al. (2011) have disclosed a distinct improvement in the synthesis of pyranocoumarin derivatives through a pericyclic approach. This route offers a valid alternative to the standard industrial synthesis for 3,4-dihydropyranocoumarins 112 were obtained by a hetero Diels–Alder (HDA) with inverse electron demand between 1, aromatic aldehydes 110 (such as benzaldehyde, 4-chlorobenzaldehyde, 4-nitrobenzaldehyde, and 2-furancarboxaldehyde) and electron-rich alkenes 111 (Scheme 60).

Tietze et al. (2001) concluded that a multicomponent domino Knoevenagel/hetero-Diels–Alder reaction of 1 with an amino aldehyde 113 and benzyl enol ethers 114, in toluene in the presence of catalytic amounts of ethylenediammonium diacetate (EDDA) and trimethyl orthoformate as dehydrating agent in an ultrasonic bath at 50 °C affords a benzyl-protected acetal 115 (Scheme 61).

Reaction of 1 with allene 116 in tetrahydrofuran in the presence of tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] afforded 3,4-dihydro-2,2-dimethyl-3-methylenepyrano[3,2-c]chromen-5(2H)-one 117 (Grigg et al., 2001) (Scheme 62).

3.2.7.4

3.2.7.4 6H,11H-[2]Benzopyrano[4,3-c][1]benzopyran-11-one

The reaction of 2-(bromomethyl)phenyllead triacetate 118 with 1 carried out in the presence of a combination of o-phenanthroline-potassium t-butoxide (3:1) as a base for reductive coupling gave 6H,11H-[2]benzopyrano[4,3-c][1]benzopyran-11-one 119 (Ganina et al., 2005; Naumov et al., 2005) (Scheme 63).

3.2.8

3.2.8 Benzopyrano[4,3-d]pyrimidines

3.2.8.1

3.2.8.1 Using conventional heating

4-Aryl-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-2,5-diones/pyrimidine-thione-5-ones 121 were prepared by reacting 1 with aromatic aldehydes 56 and urea/thiourea 120 in ethanol in the presence of concentrated hydrochloric acid, but this procedure requires prolonged heating of the reaction mixture and tedious workup and gives low yields of the products (Brahmbhatt et al., 1999) (Scheme 64).

3.2.8.2

3.2.8.2 Solution phase synthesis

Due to short reaction times, high yields and easy work-up procedures combined with the use of the multiple synthesizer, Sabitha et al. (2003) found that three component condensation of 1, an aromatic aldehyde 56, and urea (thiourea) 120 in refluxing acetonitrile containing a catalytic amount of VCl₃ gave the dihydropyrimidinones 122 with high purity >95%. (Scheme 65).

3.2.8.3

3.2.8.3 Microwave irradiation

Acidic solid support coupled with microwave is an appropriate method for the synthesis of 4-substituted benzopyrano[4,3-d]pyrimidine derivatives 123 in a few seconds with improved yield as compared to conventional heating. The main advantage being that solid supports do not absorb microwaves at 2450 MHz, so are not an obstacle for the transition of microwaves to the reactants. In addition, the limitations of the MWI assisted reaction in solvents, namely, the development of high pressure and the need for specialized sealed vessels are circumvented via this solid state technique which enables organic reactions to occur rapidly at atmospheric pressure. Montmorillonite K10 clay is a better support as compared to silica gel and acidic alumina in terms of yield and time for the synthesis of benzopyranopyrimidines 123 (Kidwai and Sapra, 2002) (Scheme 66).

Kidwai et al. (2006) developed a highly efficient environmentally benign method is proposed for the synthesis of benzopyranopyrimidines 124 apart from acidic solid support by reaction of 1 with aldehydes 56 and urea or thiourea 120 in the absence of a solvent under microwave irradiation in a few minutes gave the desired products in 90–95% yields. The proposed procedure utilizes neither solvents nor solid support nor acid catalyst, requires no special equipment, improves the product yield and shortens the reaction time and minimizes hazardous pollution (Scheme 67).

3.2.9

3.2.9 Benzopyranobenzothiazinones

One of the most successful strategies for constructing of 6,12-dihydro-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one 126, new agents with estrogenic activity mediated by estrogen receptors (ER), is the condensation and oxidative cyclization of substituted 2-aminobenzenethiol 125 with 1 in dimethyl sulfoxide at 140–150 °C (Aguirre-Pranzoni et al., 2011; Anary-Abbasinejad et al., 2008; Gupta et al., 2004; Gupta and Gupta, 2009 ) (Scheme 68).

3.2.10

3.2.10 Chromeno[3,4-e][1,3]oxazine

Vovk et al. (2007) have described the reaction of 1 with 1-chlorobenzyl isocyanates 127 occurred in anhydrous toluene at 60 °C, did not require the presence of an organic base, and led to the formation of 4-aryl-3,4-dihydro-2H,5H-chromeno[3,4-e][1,3]oxazine-2,5-diones 128 in 67–75% yields (Scheme 69).

However, 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates 129 reacted with 1 in the presence of triethylamine in toluene gave 2-aryl-2-trifluoromethyl-2,3-dihydro-4H,5H-chromeno-[3,4-e][1,3]oxazine-4,5-diones 130 (Vovk et al., 2007) (Scheme 70).

Hassanabadi et al. (2011) concluded that the reaction of acid chlorides 131 and ammonium thiocyanate 132 with 1 in the presence of N-methylimidazole led to oxazine derivatives 133 in excellent yields. The present procedure has the advantage that the reaction is performed under neutral conditions and the starting material can be used without any activation or modification (Scheme 71).

3.2.11

3.2.11 Pyrano[3,4-e][1,4,3]oxathiazines

Cablewski et al. (2007) investigated the regioselective reaction of 1 with N,N-dialkyl-N′-chlorosulfonylchloro formamidines 134 in the presence of N,N′-dimethyl-N,N′-propylene urea (DMPU) afforded 3-dialkylamino-1,1,8-trioxo-1H-6-pyrano[3,4-e][1,4,3]oxathiazines 135 (Scheme 72).

3.3

3.3 [7-6] Ring system

3.3.1

3.3.1 Benzopyrano[1,3]diazepines

Kidwai et al. (2007) have shown that a simple and facile synthesis of 7-arylbenzopyrano[1,3]diazepines 137 was accomplished by the treatment of 1, aromatic/heteroaromatic aldehydes 56, and cyanoguanidine 136 using molecular iodine as a novel catalyst in acetonitrile under reflux. This method not only provides an excellent complement to benzopyrano[1,3]diazepines 137 but also avoids the multistep and harsh reaction conditions (Scheme 73).

4 Conclusion

The present review is a summary of progress in 4-hydroxycoumarin as a versatile synthetic building block to the synthesis of all sorts of heterocycles or fused heterocycles. Even though a lot of progress has reported, We hope more astonishing applications of this compound will be revealed in the near future, and that this review may light a candle in organic chemistry.

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Introduction

Synthesis of monocyclic heterocyclic compounds

Synthesis of five-membered systems with two heteroatoms
Synthesis of five-membered ring systems with more than two heteroatoms
Synthesis of six-membered heterocycles containing one heteroatom
Synthesis of seven-membered heterocycles containing two heteroatoms

Synthesis of fused heterocyclic compounds

[5-6] Ring system
Fused [6-6]ring system
[7-6] Ring system

Conclusion

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Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity

Abstract

Abstract

Keywords

4-Hydroxycoumarin

Annelated heterocycles

Multicomponent reactions

Green chemistry

1 Introduction

2 Synthesis of monocyclic heterocyclic compounds

2.1 Synthesis of five-membered systems with two heteroatoms

2.1.1 Pyrazolin-5-ones

2.1.2 Imidazol-2(3H)-ones

2.1.3 1,2-Benzisoxazoles

2.2 Synthesis of five-membered ring systems with more than two heteroatoms

2.2.1 Dithiazoles

2.3 Synthesis of six-membered heterocycles containing one heteroatom

2.3.1 Quinoline

2.4 Synthesis of seven-membered heterocycles containing two heteroatoms

2.4.1 1,4-Diazepines

3 Synthesis of fused heterocyclic compounds

3.1 [5-6] Ring system

3.1.1 Pyrano[4,3-d]oxazol-4-ones

3.1.2 Oxathiolo[5,4-c]-2H-chromen-4-ones

3.1.3 Dihydrofuran and furocoumarins

3.1.3.1 Oxidative cycloaddition reaction mediated by metal salts

3.1.3.1.1 Using Ag (I)

3.1.3.1.2 Using Ce(IV)

3.1.3.1.3 Ruthenium(II)

3.1.3.1.4 Manganese(III) acetate

3.1.3.1.5 Multicopper oxidases (Laccases)

3.1.3.2 [4+1] Cycloaddition reaction followed by a [1,3]-H shift

3.1.3.3 Multicomponent reactions

3.1.3.3.1 Using of conventional synthesis

3.1.3.3.2 Using of microwave irradiation

3.1.3.3.3 Using of water

3.1.3.3.4 Using of solvent-free synthesis

3.1.3.3.5 Using combination of solvent-free supported reagents and microwave

3.1.3.4 Using of electrochemical routes

3.2 Fused [6-6]ring system

3.2.1 Benzopyrano[2,3-b]pyridine

3.2.2 Pyrido[3,2-c]coumarins

3.2.3 Chromeno[3,4-b][4,7]phenanthroline

3.2.4 Chromeno[4,3-b]benzo[f]quinolin-6-one

3.2.5 Pyrano benzopyrans

3.2.5.1 2H,5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione

3.2.5.1.1 Using alkyl-2-substituted-3-dimethyl-aminopropenoates

3.2.5.1.2 Using substituted-tetrahydrofuran-2-one or oxopyrrolidine

3.2.5.1.3 Using Pechmann-Duisberg reaction

3.2.5.1.4 Using double catalytic activation conditions

3.2.5.2 Synthesis of amino-substituted pyranopyranones

3.2.5.2.1 Two-component condensation

3.2.5.2.2 Three component condensation

3.2.6 3,4-Dihydro-2H,5H-1-benzopyrano[4,3-b]pyran-5-one

3.2.7.4 6H,11H-[2]Benzopyrano[4,3-c][1]benzopyran-11-one

3.2.8 Benzopyrano[4,3-d]pyrimidines

3.2.8.1 Using conventional heating

3.2.8.2 Solution phase synthesis

3.2.8.3 Microwave irradiation

3.2.9 Benzopyranobenzothiazinones

3.2.10 Chromeno[3,4-e][1,3]oxazine

3.2.11 Pyrano[3,4-e][1,4,3]oxathiazines

3.3 [7-6] Ring system

3.3.1 Benzopyrano[1,3]diazepines

4 Conclusion

References

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