Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis

Moaz M. Abdou

doi:10.1016/j.arabjc.2014.11.021

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Review

11 (

); 1061-1071

doi:

10.1016/j.arabjc.2014.11.021

Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis

Moaz M. Abdou^⁎

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

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

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

Received: 2014-6-2, Accepted: 2014-11-3, Published: 2014-11-01

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

This review presents a systematic and comprehensive survey of the utility of 4-hydroxy-2(1H)-quinolone as a building block of heterocyclic compounds. The reaction mechanism is considered as well as the scope and limitation of the most important of these approaches are demonstrated.

Keywords

4-Hydroxy-2(1H)-quinolone

Heterocycles

Microwave irradiation

Ionic liquid

Multicomponent reactions

Electrochemical routes

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1 Introduction

4-Hydroxy-2(1H)-quinolone is a versatile and convenient precursor for the synthesis of a wide variety of heterocyclic compounds (Ghandi et al., 2013; Guo et al., 2013; Abbaspour-Gilandeh et al., 2013; Neve et al., 2014; Hoecker and Gademann, 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. This new methodology based on automatic, high-tech synthetic methods enables synthesis of a large number of novel organic compounds as subjects for biological screening.

In continuation of our research program in exploring the utilization of cyclic 1,3-diketone compounds as simple precursors to privileged heterocyclic motifs (Abdou, 2017a, 2017d, 2017c, 2013a, 2013b; Abdou et al., 2013, 2012a, 2012b, 2012c; Metwally et al., 2013, 2012a, 2012b ), the first part of this review article (Abdou, 2017b) is concerned with the progress in 4-hydroxy-2(1H)-quinolone chemistry and deals with the synthesis, chemical reactivity and reactions of 4-hydroxy-2(1H)-quinolone. This second part systematizes the application of 4-hydroxy-2(1H)-quinolone in heterocyclic synthesis. The enolic reactive center in this compound provides ample opportunities to synthesize a great variety of novel compounds under relatively mild conditions and using simple laboratory equipment. Thus, the two parts are complementary and display current trends in 4-hydroxy-2(1H)-quinolone chemistry.

In the literature survey, the reactions involving 4-hydroxy-2(1H)-quinolone occur with 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 numbers and letters and the numbering of the heterocyclic ring systems is that reported by chemical abstracts.

2 Synthesis of fused heterocyclic compounds

2.1

2.1 [6-6-5] ring system

2.1.1

2.1.1 Dihydrofuran and furoquinolinones

Dihydrofuroquinolinone and furoquinolinone alkaloids are widely distributed in nature (Subramanian et al., 1992; Shobana and Shanmugam, 1986; Shobana et al., 1988; Ukrainets et al., 2006 ). They are primarily isolated from Rutaceae species as an angularly and linearly fused structure. They are reported to have various biological activities such as antimicrobial, antimalarial, insecticidal, antineoplastic, antidiuretic, antiarrhythmic and sedative (Wolters and Eilert, 1981; Svoboda et al., 1966; Basco et al., 1994 ). This wide range of biological properties has stimulated interest in the synthesis of dihydrofuroquinolinone and furoquinolinone derivatives. A number of synthetic approaches to dihydrofuroquinolinones and furoquinolinones have been well reported (Senboku et al., 1996; Suginome et al., 1990, 1991; Rao and Darbarwar, 1989; Neville et al., 1991; Grundon and Surgenor, 1978 ).

2.1.1.1

2.1.1.1 Oxidative cycloaddition reaction mediated by metal salts

The oxidative addition reaction of carbon-centered radicals to alkenes mediated by metal salts Ag(1), Ce(IV) and Mg(II) has received considerable attention over the last decade in organic synthesis for the construction of carbon–carbon bonds.

2.1.1.1.1

2.1.1.1.1 Using Ag (1)

Lee et al. (2000) have reported that a facile and simple method for the synthesis of dihydrofuran, 2-ethoxy-3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 3, is mediated by the oxidative cyclization of 4-hydroxy-2(1H)-quinolone 1 with ethyl vinyl ether 2 and silver(I)/Celite (Fetizon reagent) in acetonitrile under reflux (Scheme 1).

Although the exact mechanism of the reaction is not clear yet, it is best described as shown in Scheme 2. The starting material 1 is first oxidized by one equivalent of Ag(I) to generate the radical 4, which then attacks olefin 2 to give the radical adduct 5. The adduct 5 now undergoes fast oxidation by another one equivalent of Ag(I) to a carbocation 6. Cyclization of the carbocation 6 furnishes intermediate 7, whose deprotonation affords the product 3 (Scheme 2).

2.1.1.1.2

2.1.1.1.2 Using Ce(IV)

There has been a considerable interest in the use of CAN oxidation reactions in ionic liquids. Hence, reaction of 1 with α-methylstyrene 8 and cerium(IV) ammonium nitrate (CAN) mediated 1-n-butyl-3-methylimidazolium tetrafluoroborate[bmim][BF₄]-dichloromethane (1:9), gave tricycles 9,10 (Bar et al., 2003) (Scheme 3).

2.1.1.1.3

2.1.1.1.3 Manganese(III) acetate

Mn(III)-based oxidative radical cyclization of 4-hydroxy-2(1H)-quinolone 1 with 1,1-diphenylethene 11 in boiling glacial acetic acid afforded 3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 12 (Kumabe and Nishino, 2004) (Scheme 4).

Despite the uncertainty related to the reaction mechanism, the authors point toward manganese(III) that could oxidize tertiary carbon radical 14 to afford the corresponding carbocations 15, 16 which were converted into compound 12 (Scheme 5).

A similar, manganese(III)-mediated reaction using 4-hydroxy-2(1H)-quinolone 1 and the alkenes 17 in [bmim][BF₄]–dichloromethane gave a 1:1 mixture of the angular and linear tricycles 18 and 19, respectively (Bar et al., 2001a,b) (Scheme 6).

2.2

2.2 [6-6-5] ring system

Laccase (Agaricus bisporus)-catalyzed domino reaction of 4-hydroxy-2(1H)-quinolone 1 with catechols 20 using aerial oxygen as the oxidant delivers for the synthesis of 10-substituted 8,9-dihydroxybenzofuro[3,2-c]quinolin-6(5H)-ones 21 as single regioisomers with yields ranging from 61% to 77% (Hajdok et al., 2009) (Scheme 7). Some of these compounds have been made accessible by other methods, including tyrosinase-catalyzed oxidation, electrochemical oxidation or crude peroxidase from onion solid waste (Pandey et al., 1989; Tabakovic et al., 1983; Angeleska et al., 2013 ).

The reaction is postulated to proceed through a domino process involving several steps (Scheme 8). Initially, the laccase-catalyzed oxidation of the catechol 20 with O₂ to benzoquinone 22, which then undergoes an intermolecular 1,4-addition with the enol of 1 as a nucleophile to yield 23. A second laccase-catalyzed oxidation to the quinone intermediate (24) which further undergoes an intramolecular 1,4-addition to produce the final tetracyclic heterocycles.

2.3

2.3 Fused [6-6-6] ring system

2.3.1

2.3.1 Quinolino[4,3-b]benzo[f]quinolin-6-one

A short and simple synthesis of quinolino[4,3-b]benzo[f]quinoline derivatives 27 was accomplished in high yields via the reaction of N-benzilidenenaphthalen-2-amines 26 and 4-hydroxy-2(1H)-quinolone 1 in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) (Wang et al., 2005) (Scheme 9).

Though the detailed mechanism of the above reaction has not been clarified yet, the formation of 27 can be explained by the possible mechanism presented in Scheme 10.

2.3.2

2.3.2 Pyranoquinolines

Pyranoquinolines are the main constituent unit of the many of the alkaloids of the plant family Rutaceae (Manske and Rodrigo, 1988; Sainsbury, 1978; Chen et al., 1997; Wabo et al., 2005; Michael, 2002, 2003, 2004, 2005 ) and have gained much importance because of their interesting pharmacological properties and synthetic applications (Chen et al., 1994; Barr et al., 1995; Nahas and Abdel-Hafez, 2005; Amin, 1993; Magesh et al., 2004; Schiemann et al., 2007 ).

2.3.2.1

2.3.2.1 Angular pyranoquinolines

2.3.2.1.1

2.3.2.1.1 Pyrano[3,2-c]quinoline-2,5(2H,6H)-diones

Many methods for the synthesis of pyrano[3,2-c]quinoline-2,5(2H,6H)-dione derivatives have been reported successively. It has been reported that the preparation of 3-acetyl(benzoyl)amino-5,6-dihydropyrano[3,2-c]quinoline-2,5(2H,6H)-dione 34 was accomplished by the treatment of methyl 2-acetyl(benzoyl)amino-3-(N,N-dimethylamino)propenoates 33 with 1 in acetic acid (Ngadjui et al., 1992; Kralj et al., 1997) (Scheme 11).

An elegant and efficient one-pot synthesis of acylamino derivatives of quinoline 37 was achieved by the reaction of 35, triethyl orthoformate (TOF) 36 and 4-hydroxy-2(1H)-quinolone 1 in acetic anhydride (Kmetic et al., 1993) (Scheme 12).

Kepe et al. (1995) observed that treatment of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone 38 with 1 under basic conditions in boiling mixtures of pyridine and triethylamine led to N-(5,6-dihydro-2,5-dioxo-2H-pyrano[3,2-clquinoline-3-yl)benzamide 39 [50] (Scheme 13).

4-Hydroxy-2(1H)-quinolone 1 when condensed with ethyl-2,3-dihydro-3-oxobenzofuran-2-carboxylate 40 afforded the corresponding 6H,12H-benzofuropyrano[3,2-c]quinoline-6,12-diones 41 (Kepe et al., 1992) (Scheme 14).

Reaction of ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate 42, with 4-hydroxy-2(1H)-quinolone 1 led to the corresponding 2,5-dioxo-5,6-dihydro-pyrano[3.2-c]quinolines 43 exhibiting remarkable visible fluorescence (Mulwad et al., 1999) (Scheme 15).

Schmidt and Junek (1978) have reported the synthesis of pyrano[3,2-c]quinoline-2,5-diones 45 via the treatment of 4-hydroxy-2(1H)-quinolone 1 with 1-ethoxycarbonylethyliden 44 in nitrobenzene (Scheme 16).

The Pechmann-Duisberg reaction was employed by Kappe and Mayer (1981) to synthesize pyrano[3,2-c]quinoline-2,5-diones 47 via condensation of 1 with β-ketoesters 46 and ammonium acetate at 200 °C in nitrobenzene (Scheme 17). Also, this reaction can be performed in pyridine instead of nitrobenzene.

2.3.2.1.2

2.3.2.1.2 2-Aminopyrano[3,2-c]quinolin-5-ones

Using two component condensation:

A number of publications (Kumar and Rajendran, 2004; Dodia and Shah, 2001) have been taken out for Michael reactions of 4-hydroxy-2(1H)-quinolone 1 with various substituted acrylonitriles 48 in the presence of base (triethylamine or piperidine) as a catalyst resulting in the corresponding 2-amino-4-aryl-1,4,5,6-tetrahydro-pyrano[3,2-c]quinolin-5-ones 49 (Scheme 18).

Using three component condensation:

There have been several methods for synthesizing pyranoquinoline derivatives, including the three-component reaction of 4-hydroxy-2(1H)-quinolone 1, aldehydes 50, malononitrile for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 catalyzed by TEBA (benzyltriethylammonium chloride), piperidine, TsOH, NH₂SO₃H, SiO₂–NaHSO₃, ZnCl₂, MgCl₂, Cu (ClO₄)₂-6H₂O, Et₃N, DBU, imidazole, ammonium acetate, KF–Al₂O₃ and Yb(OTf)₃) (Sowellim et al., 1995, 1996; Wang et al., 2004a,b, 2006; Nasseri and Sadeghzadeh, 2013; Lei et al., 2011; Peng et al., 2005; Kumar et al., 2009 ) (Scheme 19). Recently, Guan et al. (2013) found that 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 could be prepared without catalyst in a mixed solvent of ethanol and water.

The condensation of 1, aldehyde 50, malononitrile 51 may occur by a mechanism of Knoevenagel condensation, Michael addition, intramolecular cyclization, and isomerization. Initially, intermediate 53 is formed by Knoevenagel condensation of aldehyde 50 and malononitrile 51 by the action of ammonium acetate. Then, the proton of 4-hydroxy-2(1H)-quinolone 1 is abstracted by ammonium acetate to form intermediate 54. Michael addition of intermediate 54 on 53 leads to the formation of 55, followed by cyclization and isomerization, affords the corresponding 2-amino-4H-pyrano[3,2-c]quinolin-5(6H)-one derivatives 52 (Wang et al., 2004a,b) (Scheme 20).

2.3.2.1.3

2.3.2.1.3 3,4-Dihydrobenzopyrano[3,2-c]quinoIin-5(6H)-one

2,2-Dimethyl-3,4-dihydropyrano[3,2-c]quinoIin-5(6H)-one 60 was prepared by refluxing a solution of l with para-formaldehyde 58 and 3,3-dimethylacrylic acid 59 in 1,4-dioxane under nitrogen atmosphere for 4.5 h (Suresh et al., 2005) (Scheme 21).

2,3,4,6-Tetrahydro-2-hydroxy-4-methylpyrano[3,2-c]quinolin-5-one 62 are synthesized from 4-hydroxy-2(1H)-quinolone 1 by tandem Knoevenagel condensation with an acetaldehyde 61 in the presence of diethylamine as a base in refluxing benzene (Ye et al., 1999) (Scheme 22).

The possible mechanism could account for the formation of product 62 via base-catalyzed condensation of a quinolinone 1 with an acetaldehyde 61 yielding the corresponding 4-hydroxy-3-(1-hydroxyethyl)quinolin-2-one 64, which is dehydrated on heating in the basic reaction medium to furnish the highly electrophilic quinone methide intermediate 65. The quinone methide 65 then undergoes competitive Michael-type addition of the enamine proceeds in a 1,4-fashion and results in an intramolecular cyclization to give the 2-(diethylamino)pyrano-[3,2-c]quinolin-5-one 66, which on hydrolysis during the reaction affords the final product 62 (Scheme 23).

An efficient synthesis of pyranoquinoline alkaloids is described by Thangavel et al. (2007) via direct treatment of isoprene 68 with 4-hydroxy-2(1H)-quinolone 1 in the presence of polyphosphoric acid, furnishing dihydroflindersine 69 in good yield (Scheme 24).

2.3.2.1.4

2.3.2.1.4 Miscellaneous pyrono quinolone

In water medium, environmentally benign, facile, and efficient synthesis of pyrans 71 was achieved in good yields by domino Knoevenagel reaction of 1 with several α,β-unsaturated aldehydes 70 (Jung et al., 2010) (Scheme 25). This method has been successfully applied to the synthesis of biologically interesting and naturally occurring pyranoquinolinone alkaloids in good yields. Also, this reaction can be achieved by ytterbium(III) triflate (Lee et al., 2001) or ethylenediaminediacetic acid in dichloromethane (Wang and Yong, 2007).

2.3.2.3

2.3.2.3 Linear pyranoquinolines

Nöhammer and Kappe (1976) showed that the reaction of 4-hydroxy-2(1H)-quinolone 1 with malonyl chlorides 72 in the presence of N,N-dimethylaniline 73 yielded the corresponding linear pyronoquinolones 74 (Scheme 26).

Sangeetha and Prasad (2006) adopted a novel and highly efficient methodology for synthesizing quinolino[2,3-o]carbazolo[6,5-a]pyran-7,8-diones 77 with interesting biological activity via reaction of 1 with vinyl acetate 75 and 3,11-dihydro-2,4-dioxopyrano[2,3-o]carbazoles 76 (Scheme 27).

2.3.3

2.3.3 Quinolinobenzothiazinones

One of the most successful strategies for constructing 5H-quinolin[3,4-b][1,4]benzothiazin-6(12H)-one 79 as a new agent with estrogenic activity mediated by estrogen receptors (ER) is the condensation and oxidative cyclization of amino thiophenol 78 with 1 in dioxane in the presence of p-toluene sulfonic acid (Ruano et al., 1991) or N,N-dimethylformamide (Coppola et al., 1981) (Scheme 28).

2.4

2.4 [6-6-8-6] ring system

2.4.1

2.4.1 Oxazocines

Basic alumina supported and solvent-free synthesis of novel oxazocines 81 has been achieved in excellent yields by tandem C-alkylation followed by intramolecular O-alkylation of 1 with quinolinium salts 80 under microwave irradiation (Mondal et al., 2011) (Scheme 29).

3 Conclusion

The data considered in this review clearly demonstrate that 4-hydroxy-2(1H)-quinolone may be successfully used to synthesize a wide variety of heterocycles of academic and pharmaceuticals interest. Finally, all chemistry presented here along with that already discussed in my previous review article (Abdou, 2017b), clearly demonstrates the utility of 4-hydroxy-2(1H)-quinolone for countless organic transformations.

Acknowledgements

It is a pleasure to acknowledge the contributions made by my co-workers mentioned in the list of references. For financial support, I would like to thank the Academy of Scientific Research and Technology, ASRT, Egypt. Also, the author regrets any omissions that may have occurred in this review. Finally, I would like to thank Professor El-Sayed I. El-Desoky for reading the manuscript and making useful suggestions.

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Introduction

Synthesis of fused heterocyclic compounds

[6-6-5] ring system
[6-6-5] ring system
Fused [6-6-6] ring system
[6-6-8-6] ring system

Conclusion

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Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis

Abstract

Keywords

4-Hydroxy-2(1H)-quinolone

Heterocycles

Microwave irradiation

Ionic liquid

Multicomponent reactions

Electrochemical routes

1 Introduction

2 Synthesis of fused heterocyclic compounds

2.1 [6-6-5] ring system

2.1.1 Dihydrofuran and furoquinolinones

2.1.1.1 Oxidative cycloaddition reaction mediated by metal salts

2.1.1.1.1 Using Ag (1)

2.1.1.1.2 Using Ce(IV)

2.1.1.1.3 Manganese(III) acetate

2.2 [6-6-5] ring system

2.3 Fused [6-6-6] ring system

2.3.1 Quinolino[4,3-b]benzo[f]quinolin-6-one

2.3.2 Pyranoquinolines

2.3.2.1 Angular pyranoquinolines

2.3.2.1.1 Pyrano[3,2-c]quinoline-2,5(2H,6H)-diones

2.3.2.1.2 2-Aminopyrano[3,2-c]quinolin-5-ones

2.3.2.1.3 3,4-Dihydrobenzopyrano[3,2-c]quinoIin-5(6H)-one

2.3.2.1.4 Miscellaneous pyrono quinolone

2.3.2.3 Linear pyranoquinolines

2.3.3 Quinolinobenzothiazinones

2.4 [6-6-8-6] ring system

2.4.1 Oxazocines

3 Conclusion

Acknowledgements

References

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