Synthesis of quinoxaline derivatives using sulfonic acid functionalized imidazolium salts as highly efficient and reusable bronsted acidic ionic liquids catalysts under solvent free conditions sami sajjadifar, eshagh rezaee nezhad and ehsan khosravani department of chemistry, payame noor university, p o box 193954697, tehran, iran. In specific you are using a safe substance thiamine, vitamin b1 as a catalyst. In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. Synthesis of quinoxaline derivatives over highly efficient and reusable bronsted acidic ionic liquids. They can be formed by condensing orthodiamines with 1,2diketones.
The classical synthesis of quinoxaline derivatives involves the double condensation of aryl 1,2diamines with 1,2. An efficient protocol for the synthesis of quinoxaline. Zhou jf, gong gx, shi kb, zhi sj 2009 catalyst free and solvent free method for the synthesis of quinoxalines under microwave irradiation. An efficient catalystfree protocol for the synthesis of quinoxaline. Quinoxalinedione is an organic compound with the formula c 6 h 4 nh 2 co 2. Efficient synthesis of quinoxaline derivatives catalyzed. Green chemistry approaches for the synthesis of quinoxaline derivatives.
We have synthesized quinoxaline analogs 125, characterized by 1hnmr and hreims and evaluated for thymidine phosphorylase inhibition. Heravi et al oiodoxybenzoic acid ibx, a readily available hypervalent iodine v reagent, was found to be highly effective in synthesis of quinoxaline derivatives, from 1,2diketones and ophenylenediamines at room. The quinoxaline moiety is present in a large variety of physiologically active compounds, with applications varying from medicinal to agricultural. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. Onepot threecomponent synthesis of quinoxaline and. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Among the series, nineteen analogs showed better inhibition when compared with the standard inhibitor 7deazaxanthine ic50 38. Onepot threecomponent coupling of oalkynylheteroaryl carbonyl derivatives with fischer carbene complexes and dienophiles leading to the synthesis of quinoxaline and phenazine ring systems has been investigated. Synthesis of quinoxalines promoted by ecofriendly nanokaoline.
Heterocyclic compounds are a class of substances, which play a critical role in modern drug discovery being incorporated in the structure of a large variety. Abstract a green and efficient procedure for the synthesis of quinoxalines is reported starting from benzil and 1,2diaminobenzene. Synthesis, reactions and biological activity of quinoxaline derivatives. Chemistry department, faculty of science, jazan university, saudi arabia. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2diaminobenzene. Efficient and practical protocol for the synthesis of pyridopyrazines. A convenient synthesis of substituted quinoxalines in good yields from ophenylenediamines and ynones via michael addition, dehydration condensation, and basepromoted c. Quinoxalinediones are a family of related compounds sharing the same bicyclic core. Thus, a series of 18 such derivatives have been synthesized, characterized on the basis of spectroscopic method and were tested for their antimicrobial activity against staphylococcus aureus staph. Synthesis and antimicrobial activities of some novel. Design and synthesis of new quinoxaline derivatives as. Lproline as an e cient organocatalyst for the synthesis of quinoxaline derivatives under solvent free conditions a.
In this laboratory experience you will examine the synthesis of heterocyclic molecules. Twentynine new 67substituted quinoxaline 2carboxylate 1,4dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. It is a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine. A convenient process of preparing of 2,3 diphenyl quinoxaline derivatives. This involves the generation of furo3,4bpyrazine and furo3,4b quinoxaline as transient intermediates, which were trapped with dielsalder dienophiles. Efficient synthesis of quinoxaline derivatives catalyzed by ptoluenesulfonic acid under solventfree conditions. It is a colorless solid that is soluble in polar organic solvents. The regioselectivity in their dielsalder cycloaddition reactions. Cancer, drug discovery, synthesis, quinoxaline, heterocyclic compounds, biological activity. Numerous methods are available for the synthesis of quinoxaline derivatives which.
Pdf a catalystfree expeditious green synthesis of quinoxaline. An efficient synthesis of quinoxaline derivatives catalyzed by ptoluene sulfonic acid under solventfree conditions was reported by shi and dou 86 scheme. Lproline as an e cient organocatalyst for the synthesis. Pdf a convenient process of preparing of 2,3 diphenyl. Efficient synthesis of quinoxaline derivatives catalyzed by p. View notes ch 11 benzil quinoxaline synthesis report from chem 255 at ohio state university. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the.
Ecofriendly approach to access of quinoxaline derivatives. Pdf facile method of quinoxaline synthesis using phenol. Quinoxaline article about quinoxaline by the free dictionary. A series of quinoxaline derivatives were efficiently synthesized in excellent yields by the reaction of 1,2diamines and 1,2diketones with grinding catalyzed by ptoluenesulfonic acid under solvent free conditions at room temperature. Comparison of ethanol and water in the presence of the reusable catalyst cellulose sulfuric acid. Under the rhiii catalyst, reaction proceeded through the free amine assisted c2. Wong and coworkers have studied quinoxaline derivatives theoretically12. Highly efficient synthesis of quinoxaline derivatives from.
An efficient catalystfree protocol for the synthesis of quinoxaline derivatives under. Chromophorelabeled quinoxaline derivatives as efficient. An efficient protocol for the synthesis of quinoxaline derivatives at. Ch 2extrusion under metal free conditions features high regioselectivity, efficiency, and environmental friendliness. Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2dicarbonyl compounds in the presence of ibx in acetic acid. Onepot and efficient protocol for synthesis of quinoxaline derivatives mohammad reza islami and zahra hassani department of chemistry, shahid bahonar university, kerman, iran p. 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. A greener chemistry approach for synthesis of 2,3diphenyl quinoxaline.
A facile synthesis of quinoxaline quinones is reported. The synthesis and chemistry of quinoxalines have attracted considerable attention in the past 10 years. A green protocol for the synthesis of quinoxaline derivatives catalyzed by polymer supported sulphanilic acid. A greener chemistry approach for synthesis of 2,3diphenyl. The solvent free synthesis of quinoxalines using the sulfonic acid functionalized imidazolium salts. Consequently, a large variety of synthetic methods for the synthesis of functionalized quinoxalines have been reported in literature. Synthesis of quinoxaline quinones and regioselectivity in. Pdf on apr 9, 2019, ankush mishra and others published a catalystfree expeditious green synthesis of quinoxaline, oxazine, thiazine. It is rare in natural state, but their synthesis is easy to perform. Compared with the classical synthetic method, this new method has the advantages of convenient manipulation and environmental friendliness. Progress in quinoxaline synthesis part 2 request pdf. This method had many dramatic advantages, such as the short reaction time 26 min, high yields 7198%, and. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented.
Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. A series of new quinoxaline derivatives of dehydroabietic acid daa were designed and synthesized as potential antitumor agents. As part of our ongoing research on the development of alternative synthetic procedures for the synthesis of biologically active heterocyclic compounds and the use of green chemistry techniques in organic synthesis, herein we report a simple and efficient method for the preparation of quinoxaline derivatives using heteropolyacids hpmo 11 vfeo 40. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline. Synthesis of new quinoxaline2carboxylate 1,4dioxide. Facile method of quinoxaline synthesis using phenol as a new, efficient and cheap catalyst at room temperature. Cert if i ed that the thes is ent it led n synthesis and reactions of quinoxalines 11 submi t ted by shri keshav mohan is a bona fide work done by him under my guidance. Ionic liquid 1butyl3methylimidazolium bromide bmimbr. Based on the abovementioned antiproliferative quinoxaline compounds 15 and sorafenib as a urea derivative 18, we aimed to design a new series of quinoxaline based compounds with amide. Facile synthesis of quinoxaline derivatives using o. Pdf green chemistry approaches for the synthesis of. Pdf on apr 9, 2019, ankush mishra and others published a catalyst free expeditious green synthesis of quinoxaline, oxazine, thiazine, and dioxin derivatives in water under ultrasound irradiation. The reaction proceeds very cleanly at room temperature in a onepot procedure and free of side products. Microwaveassisted catalystfree and solventfree method.
In addition you will see some ways that green chemistry principles can be used to prepare the products more safely than has been done previously. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on. Conventionally, quinoxaline synthesis can be achieved by the reaction of 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. Highly efficient synthesis of quinoxaline derivatives from 1,2benzenediamine and. Spectrophotometric study of coii and niii complexes with quinoxaline 2,3dithiol has been reported by ayres et al 23. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman. Synthesis of quinoxaline derivatives using sulfonic acid. Photochemistry department heterocyclic unit, national research centre, giza, egypt. Quinoxaline, benzopyrazine, antimicrobial activity introduction quinoxalines, also called a benzopyrazines, in organic chemistry, it is a hetrocyclic compounds. Molecules free fulltext synthesis and evaluation of new. A novel and efficient procedure was introduced for the synthesis of alkyl acetates bearing arylthio and quinoxaline moieties from the reaction of o.
It has been observed that the presence of a chloro, methyl, or methoxy group in position 7 of the benzene moiety reduces the mic and ic50. Pdf a simple, highly efficient and green procedure for the preparation of quinoxaline in the. The solventfree synthesis of quinoxalines using the sulfonic acid. A simple and efficient protocol for the synthesis of quinoxalines. Quinoxaline derivative an overview sciencedirect topics.
The catalyst is recyclable and reusable 2006 published by elsevier b. Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. In this article we report the synthesis of quinoxaline derivatives in the presence of ibx. Benzil quinoxaline synthesis cameron trefny jason young tth 5. The method shows high yields of quinoxaline derivatives under heterogeneous conditions. The cdk15 inhibitor, also referenced under cas 40254908, controls the biological activity of cdk15. Molecules free fulltext synthesis and antimicrobial activity of. Quinoxalines and fused ring systems show diverse pharmacological activities.
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