This heterocycle can be regarded as aromatic in character and their chemistry has very little in common with benzene although their resonance. We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts. In the present study, we report the synthesis of various quinoxaline derivatives from direct condensation of substituted aromatic 1,2diamine with 1,2dicarbonyl catalyzed by nanostructured pyrophosphate na2pdp2o7 as a new highly efficient bifunctionalheterogeneous catalyst. Jan 28, 2015 quinoxaline as a potent heterocyclic 18 oxidation of quinoxaline results in the formation of the product depending on the nature of the oxidizing agent employed. Compound 1 was prepared according to previously reported procedures by condensation of commercially available 2,3dichloroquinoxaline with malononitrile in the presence of sodium hydride. With alkaline potassium permanganate pyrazine 2,3dicarboxylic acid is formed, while with peracid quinoxaline dinoxide results. Quinoxaline itself prepared by the condensation of ophenylene diamine with glyoxal sodium bisulphite in 8590% yield29. Polymer supported sulphanilic acid was found to be an effective heterogeneous catalyst for one pot synthesis of various quinoxaline derivatives from the.
Chemistry department, faculty of science, jazan university, saudi arabia. Synthesis, characterization and protonation behavior of. Synthesis and pharmacological applications of certain. The quinoxalinylglyoxal oxime 25 thus yields the 2,2bisquinoxaline 26. The present paper describes the synthesis and antibacterial activity of sixteen new quinoxaline 5. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. A number of synthetic methods are available for the synthesis of 1 and its derivatives.
A simple and efficient protocol for the synthesis of. In the synthesis, the reaction of 1,2phenylenediamines and phenacyl bromide were carried out using pyridine as a catalyst in. The chemistry and applications of the quinoxaline compounds. Facile method of quinoxaline synthesis using phenol as a. Then reaction mixture was cooled and poured into water to get sulfonamide derivative of 2, 3diphenylquinoxaline. These catalysts were prepared by incipient wetness impregnation.
Synthesis and characterization of two diastereomeric cshaped molecules containing cofacial thiophenesubstituted quinoxaline rings are described. Synthesis and evaluation of quinoxaline derivatives as. Synthesis of sulfonamide derivatives of quinoxaline synthesis of 2, 3diphenyl, 7sulfonamido quinoxaline l1 sulfonylchloride quinoxaline derivative was refluxed with 50% 30 ml nh 3 solution for 1. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in applications such as optical devices and. Synthesis of quinoxaline and its derivatives scheme 1.
The most common method is condensation of an aryl 1,2diamine with 1,2dicarbonyl compound in suitable solvent 19, 20 scheme1. Synthesis and activity of some quinoxaline analogues of. Onepot and efficient protocol for synthesis of quinoxaline derivatives. Synthesis and photophysical properties of selenopheno2,3. Synthesis and antimicrobial activities of some novel. Design of the synthesized compounds ixa,b, xviiia,b, viii a e, xvii a f and xxv. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to. This reaction proceeds via imine formation, cyclisation, and oxidation in one. Pdf the objective of present research work is to provide green technique for synthesis of 2,3diphenyl quinoxaline. Synthesis of highly functionalized polycyclic quinoxaline. The synthesis of 1hpyrrolo2,3b quinoxaline derivatives 6 and 7 is shown in scheme 1. They can be formed by condensing orthodiamines with 1,2diketones. Conventionally, quinoxaline synthesis can be achieved by the reaction of 1,2.
Transition metalfree acylation of quinoxaline derivatives, by cross dehydrogenative coupling cdc reaction, were studied. Design and synthesis of some new quinoxaline based heterocycles. Pharmaceutical chemistry department, faculty of pharmacy, alazhar university, cairo, egypt. View the article pdf and any associated supplements and figures for a period of 48 hours.
Safe and reliable synthesis of diazoketones and quinoxalines. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Synthesis, reactions and biological activity of quinoxaline derivatives. Quinoxalinebased molecules have been disclosed as the antibacterial and antiprotozoal properties. Quinoxaline as a potent heterocyclic 18 oxidation of quinoxaline results in the formation of the product depending on the nature of the oxidizing agent employed.
Chemical structures of glu, ampa, ka, nmda, and competitive antagonists ly466195, satpo, dnqx, and. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the. A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. Quinoxalines with amide and sulphonamide moieties have been reported to inhibit the growth of human tumor cell lines 8. Quinoxalines and fused ring systems show diverse pharmacological activities. Photochemistry department heterocyclic unit, national research centre, giza, egypt. Facile method of quinoxaline synthesis using phenol as a new. As a result of the annulation of the quinoxaline moiety on the porphycene skeleton, 1ah2 and 1bh2 display absorption and fluorescence in the near infrared nir region.
A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. Compounds 3a3i were obtained by the condensation of o phenylenediamines with 1,2. Synthesis of 1,4dihydro quinoxaline 2,3dione 1 1,4dihydro quinoxaline 2,3dione 1 was prepared. Recent trends in synthesis of quinoxaline and its derivatives. May 25, 2010 the synthesis of quinoxaline ring systems involves the coupling of fischer carbene complexes 2732 with 2alkynyl3pyrazine carbonyl derivatives, followed by the generation of a hitherto unknown intermediate e. S1 onepot synthesis of pyrrolo1,2a quinoxaline derivatives via a coppercatalyzed aerobic oxidative domino reaction huanhuan liu,a tiantian duan a, zeyuan zhang a, caixia xie a and chen maab aschool of chemistry and chemical engineering, shandong university, jinan 250100, p. Quinoxalines, also named as benzopyrazines, having a nitrogen ring, in organic chemistry is a hetrocyclic compounds containing a ring complex made up of a benzene ring and a pyrazine ring. They are wellknown for application in organic light emitting devices, polymers and pharmaceutical agents. Synthesis and activity of some quinoxaline analogues of streptonigrin by. Design, synthesis, optoelectrochemical and theoretical. Facile route for the synthesis and characterization of new. An efficient protocol for the synthesis of quinoxaline derivatives at.
Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline 2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. Synthesis and pharmacological applications of certain quinoxaline analogues. Spectrophotometric study of coii and niii complexes with quinoxaline 2,3dithiol has been reported by ayres et al 23. Synthesis of 4h2acetylnaphtho2,3f quinoxaline3,7,12 trione 4 a mixture of 2 2 g, 8 mmol and ethylacetoacetate 1 ml, 8 mmol in 30 ml dimethylformamide containing 0. Facile method of quinoxaline synthesis using phenol as a new, efficient and cheap catalyst at room temperature. Quinoxalines synthesis, bronsted acidic ionic liquids bails, green chemistry. China bstate key laboratory of natural and biomimetic drugs, peking university, beijing, 100191, p. Synthesis, reactions and biological activity of quinoxaline. Consequently, a large variety of synthetic methods for the synthesis of functionalized quinoxalines have been reported in literature. Quinoxaline is prepared by the reaction of ophenylenediamine with glyoxal. Quinoxaline based molecules have been disclosed as the antibacterial and antiprotozoal properties. Application quinoxaline was used in the synthesis of quinoxalinediones.
In addition, quinoxaline derivatives have been evaluated as anthelmintic agents, semiconductors, dyes and biocides. Facile synthesis of quinoxaline derivatives using o. Onepot synthesis of pyrrolo1,2aquinoxaline derivatives. Pdf green synthesis of quinoxaline derivatives researchgate. General procedure for synthesis of quinoxaline derivatives 2af. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in. Quinoxaline 2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. Ecofriendly approach to access of quinoxaline derivatives.
To synthesize benzil quinoxaline from benzil and ophenylenediamine in a condensation, double imine formation reaction. Synthesis of quinoxalines promoted by ecofriendly nanokaoline. Department of chemistry, school of advanced sciences, vit university, vellore, tamil nadu 632014, department of chemistry, school of advanced sciences, vit university, vellore, tamil nadu 632014. To modify in their nucleus, they form different derivatives of quinoxaline which contains antimicrobial activity. It is a colorless oil that melts just above room temperature. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. Quinoxalines synthesis, reactions, mechanisms and structure. Additionally, the quinoxaline moieties of 1ah2 and 1bh2 act as electronwithdrawing groups, introducing lower. Synthesis and activity of some quinoxaline analogues of streptonigrin.
Various novel, mild, ecofriendly and efficient methods have been developed for the preparation of quinoxaline derivatives in high yields. Progress in quinoxaline synthesis part 2 request pdf. An efficient protocol for the synthesis of quinoxaline. Ikk inhibitor iii, bms345541 cas 445430580 calbiochem. Synthesis, characterization, antibacterial and antifungal activities of new quinoxaline 1,4dinoxide derivatives. As potential antiinflammatory and analgesic activity. Its molecular formula is c 8h 6n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. The present study includes the synthesis of sulfonamide derivatives of quinoxaline, by additionelimination mechanism. Synthesis and evaluation of pyrazine and quinoxaline fluorophores for in vivo detection of cerebral tau tangles in alzheimers models biyue zhu, a ting zhang, a qian jiang, a ying li, a yu fu, a jiapei dai, b ge li, c qingrong qi a and yan cheng a. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsrnans1a interaction to varying extents.
Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. There are many reported procedures for the synthesis of bis and polyquinoxalines and quinoxaline containing macrocycles. Synthesis of functionalized pentamer metallonanobelts was accomplished by using a series of triptycene ligands, which were synthesized by quinoxaline formation from 2,3,6,7,14,15hexaaminotriptycene 1 as a common precursor. The present paper describes the synthesis and antibacterial activity of sixteen new quinoxaline5carboxamide derivatives 5a5p from commercially available methyl 2, 3diamino benzoate as staring material. Compound 4 consider good and available starting key to synthesis many new of quinoxaline. Onepot and efficient protocol for synthesis of quinoxaline. This work is licensed under a creative commons attributionnoncommercial 3. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2diaminobenzene. Benzil quinoxaline synthesis cameron trefny jason young tth 5. A green protocol for the synthesis of quinoxaline derivatives.
A further extension of the classical reaction sequence for quinoxaline synthesis involves the use of alicyclic or heterocyclic adicarbonyl compounds or their derivatives. Natural products containing quinoxaline ring are rare and can be easily prepared or synthesized. Furthermore, one pot synthesis of quinoxaline derivatives were prepared via reacted ophenylenediamine derivatives 1a, b, e with 1, 2dicarbonyl compounds oxalaldehyde, biacetyl, oxalyl difluoride and dimethyl oxalate respectively at room temperature by using different catalysts 7486 as cuso 4. Pdf design and synthesis of some new quinoxalinebased. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines. The quinoxaline containing polymers are applicable in optical devices due to their thermal stability and low band gap. Design and synthesis of new quinoxaline derivatives as. The synthesis of quinoxalines has been intensively studied in the past, especially because of the diverse biological activities ascribed to many representatives of this class of compounds. Cshaped diastereomers containing cofacial thiophene.
Onepot threecomponent synthesis of quinoxaline and. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in dyes1,pharmaceuticals2 and electricalphotochemical materials3. N n quinoxaline o o ch3 ch3 butane2,3dione nh2 nh2 benzene1,2diamine scheme 1. Negishi cross coupling between the 6 quinoxaline moiety and the side chain of the amino acid was planned as the key step. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. Application of a reusable cobased nanocatalyst in alcohol. Bioinspired orthoquinone catalysts have been applied to oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant. In this paper, we report the novel synthesis of three different heterocycles namely 2arylselenopheno2,3b quinoxaline, 3arylalkylselanyl2arylselenopheno2,3b quinoxaline and 6phenyl7arylselanylselenopheno2,3bpyrazine derivatives from the corresponding 2,3dichloroquinoxaline and 2,3dichloropyrazine derivatives. Synthesis and biological evaluation of new quinoxaline. The method shows high yields of quinoxaline derivatives under. Here, we have highlighted some convenient methods for quinoxaline synthesis along with their novel biological properties.
The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman and cookson in 1979. A simple and efficient protocol for the synthesis of quinoxalines. Pyrrolo3,2 bquinoxaline derivatives as types i and ii. Synthesis and evaluation of pyrazine and quinoxaline. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in dyes1 pharmaceuticals23 and electricalphotochemical materials49. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. It is rare in natural state, but their synthesis is easy to perform. Exploring biological activities of quinoxaline derivatives. Cooac 2phencarbon800 cophenc800 showed the superior reactivity compared to other materials prepared at different temperature, in the synthesis of quinoxalines by the coupling between diamines and diols. A library of quinoxaline derivatives were prepared to target nonstructural protein 1 of influenza a ns1a as a means to develop antiinfluenza drug leads. The catalyst is recyclable and reusable 2006 published by elsevier b. China bstate key laboratory of natural and biomimetic drugs, peking university, beijing. The protocol showcases an efficient inline purification using supported scavengers with timesaving and safety benefits and in particular a reduction in the. The experimental reaction conditions were o phenylenediamine, 1 mmol.
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