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. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline based molecules have been disclosed as the antibacterial and antiprotozoal properties. Chemistry department, faculty of science, jazan university, saudi arabia. Onepot threecomponent synthesis of quinoxaline and. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. Cshaped diastereomers containing cofacial thiophene. Synthesis, characterization and protonation behavior of.
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. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the. The protocol showcases an efficient inline purification using supported scavengers with timesaving and safety benefits and in particular a reduction in the. This heterocycle can be regarded as aromatic in character and their chemistry has very little in common with benzene although their resonance. 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 green protocol for the synthesis of quinoxaline derivatives. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to. Facile route for the synthesis and characterization of new. A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in dyes1 pharmaceuticals23 and electricalphotochemical materials49. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsrnans1a interaction to varying extents. Benzil quinoxaline synthesis cameron trefny jason young tth 5. Design and synthesis of some new quinoxaline based heterocycles. The present study includes the synthesis of sulfonamide derivatives of quinoxaline, by additionelimination mechanism. Facile method of quinoxaline synthesis using phenol as a. Facile method of quinoxaline synthesis using phenol as a new, efficient and cheap catalyst at room temperature.
The catalytic test was performed under different reaction conditions in order to know the performance of the synthesized catalysts. Synthesis and pharmacological applications of certain quinoxaline analogues. Synthesis and activity of some quinoxaline analogues of streptonigrin. Transition metalfree acylation of quinoxaline derivatives, by cross dehydrogenative coupling cdc reaction, were studied.
Additionally, the quinoxaline moieties of 1ah2 and 1bh2 act as electronwithdrawing groups, introducing lower. Synthesis of quinoxalines promoted by ecofriendly nanokaoline. Design, synthesis, optoelectrochemical and theoretical. Safe and reliable synthesis of diazoketones and quinoxalines. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Quinoxaline is prepared by the reaction of ophenylenediamine with glyoxal. Quinoxalines synthesis, reactions, mechanisms and structure.
N n quinoxaline o o ch3 ch3 butane2,3dione nh2 nh2 benzene1,2diamine scheme 1. A number of synthetic methods are available for the synthesis of 1 and its derivatives. Application quinoxaline was used in the synthesis of quinoxalinediones. Chemical structures of glu, ampa, ka, nmda, and competitive antagonists ly466195, satpo, dnqx, and. Compound 4 consider good and available starting key to synthesis many new of quinoxaline. 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. 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. We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts.
Pyrrolo3,2 bquinoxaline derivatives as types i and ii. 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. Pdf design and synthesis of some new quinoxalinebased. The most common method is condensation of an aryl 1,2diamine with 1,2dicarbonyl compound in suitable solvent 19, 20 scheme1.
The method shows high yields of quinoxaline derivatives under. Photochemistry department heterocyclic unit, national research centre, giza, egypt. 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. To synthesize benzil quinoxaline from benzil and ophenylenediamine in a condensation, double imine formation reaction. Synthesis, characterization, antibacterial and antifungal activities of new quinoxaline 1,4dinoxide derivatives. Synthesis and activity of some quinoxaline analogues of streptonigrin by. Consequently, a large variety of synthetic methods for the synthesis of functionalized quinoxalines have been reported in literature. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. China bstate key laboratory of natural and biomimetic drugs, peking university, beijing. Synthesis and photophysical properties of selenopheno2,3. Quinoxalines with amide and sulphonamide moieties have been reported to inhibit the growth of human tumor cell lines 8. Facile synthesis of quinoxaline derivatives using o. 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. 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.
An efficient protocol for the synthesis of quinoxaline. Progress in quinoxaline synthesis part 2 request pdf. Polymer supported sulphanilic acid was found to be an effective heterogeneous catalyst for one pot synthesis of various quinoxaline derivatives from the. In addition, quinoxaline derivatives have been evaluated as anthelmintic agents, semiconductors, dyes and biocides. Synthesis and characterization of two diastereomeric cshaped molecules containing cofacial thiophenesubstituted quinoxaline rings are described. Compounds 3a3i were obtained by the condensation of o phenylenediamines with 1,2.
A library of quinoxaline derivatives were prepared to target nonstructural protein 1 of influenza a ns1a as a means to develop antiinfluenza drug leads. Quinoxaline 2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. Synthesis and evaluation of pyrazine and quinoxaline. A further extension of the classical reaction sequence for quinoxaline synthesis involves the use of alicyclic or heterocyclic adicarbonyl compounds or their derivatives. A simple and efficient protocol for the synthesis of. Spectrophotometric study of coii and niii complexes with quinoxaline 2,3dithiol has been reported by ayres et al 23. 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.
Ikk inhibitor iii, bms345541 cas 445430580 calbiochem. China bstate key laboratory of natural and biomimetic drugs, peking university, beijing, 100191, p. Negishi cross coupling between the 6 quinoxaline moiety and the side chain of the amino acid was planned as the key step. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in applications such as optical devices and materials.
The present paper describes the synthesis and antibacterial activity of sixteen new quinoxaline 5. 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. Onepot and efficient protocol for synthesis of quinoxaline derivatives.
Then reaction mixture was cooled and poured into water to get sulfonamide derivative of 2, 3diphenylquinoxaline. General procedure for synthesis of quinoxaline derivatives 2af. Design of the synthesized compounds ixa,b, xviiia,b, viii a e, xvii a f and xxv. 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. 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 efficient protocol for the synthesis of quinoxaline derivatives at. 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. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines. To modify in their nucleus, they form different derivatives of quinoxaline which contains antimicrobial activity. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in. Synthesis of quinoxaline and its derivatives scheme 1.
Recent trends in synthesis of quinoxaline and its derivatives. Various novel, mild, ecofriendly and efficient methods have been developed for the preparation of quinoxaline derivatives in high yields. Quinoxalines and fused ring systems show diverse pharmacological activities. Synthesis of highly functionalized polycyclic quinoxaline. Pdf facile method of quinoxaline synthesis using phenol. Synthesis of 1,4dihydro quinoxaline 2,3dione 1 1,4dihydro quinoxaline 2,3dione 1 was prepared. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2diaminobenzene. 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. They can be formed by condensing orthodiamines with 1,2diketones. Synthesis and biological evaluation of new quinoxaline. Compound 1 was prepared according to previously reported procedures by condensation of commercially available 2,3dichloroquinoxaline with malononitrile in the presence of sodium hydride. Conventionally, quinoxaline synthesis can be achieved by the reaction of 1,2. Ecofriendly approach to access of quinoxaline derivatives.
Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline 2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. Application of a reusable cobased nanocatalyst in alcohol. As potential antiinflammatory and analgesic activity. Synthesis, reactions and biological activity of quinoxaline derivatives. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in dyes1,pharmaceuticals2 and electricalphotochemical materials3. The synthesis of 1hpyrrolo2,3b quinoxaline derivatives 6 and 7 is shown in scheme 1. 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. Synthesis and antimicrobial activities of some novel. This reaction proceeds via imine formation, cyclisation, and oxidation in one. The classic method for quinoxaline preparation is the condensation of a 1,2 dicarbonylic compound with a 1,2diamino compound.
Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. Onepot and efficient protocol for synthesis of quinoxaline. They are wellknown for application in organic light emitting devices, polymers and pharmaceutical agents. The chemistry and applications of the quinoxaline compounds. This work is licensed under a creative commons attributionnoncommercial 3. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. 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. 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. Here, we have highlighted some convenient methods for quinoxaline synthesis along with their novel biological properties. 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. These chapters give comprehensive coverage of all the methods of the synthesis of quinoxalines and the important quinoxalinecontaining ring systems such as thiazolo3,4a, pyrrolo1,2a, and imidazo1,5a quinoxalines. View the article pdf and any associated supplements and figures for a period of 48 hours.
These catalysts were prepared by incipient wetness impregnation. With alkaline potassium permanganate pyrazine 2,3dicarboxylic acid is formed, while with peracid quinoxaline dinoxide results. Design and synthesis of new quinoxaline derivatives as. Pdf green synthesis of quinoxaline derivatives researchgate. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. Facile method of quinoxaline synthesis using phenol as a new.
The quinoxaline containing polymers are applicable in optical devices due to their thermal stability and low band gap. 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. Its molecular formula is c 8h 6n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. 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. Quinoxaline itself prepared by the condensation of ophenylene diamine with glyoxal sodium bisulphite in 8590% yield29. 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. Exploring biological activities of quinoxaline derivatives. Onepot synthesis of pyrrolo1,2aquinoxaline derivatives. Quinoxalinebased molecules have been disclosed as the antibacterial and antiprotozoal properties. Natural products containing quinoxaline ring are rare and can be easily prepared or synthesized. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Chapter five describes many new methods for the construction of quinoxaline macrocycles, which are important in applications such as optical devices and. Synthesis, reactions and biological activity of quinoxaline.
Pdf the objective of present research work is to provide green technique for synthesis of 2,3diphenyl quinoxaline. It is rare in natural state, but their synthesis is easy to perform. Synthesis and evaluation of quinoxaline derivatives as. Pharmaceutical chemistry department, faculty of pharmacy, alazhar university, cairo, egypt. In the synthesis, the reaction of 1,2phenylenediamines and phenacyl bromide were carried out using pyridine as a catalyst in. The catalyst is recyclable and reusable 2006 published by elsevier b. The experimental reaction conditions were o phenylenediamine, 1 mmol. Quinoxalines synthesis, bronsted acidic ionic liquids bails, green chemistry. The quinoxalinylglyoxal oxime 25 thus yields the 2,2bisquinoxaline 26. There are many reported procedures for the synthesis of bis and polyquinoxalines and quinoxaline containing macrocycles. Synthesis and activity of some quinoxaline analogues of.
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