In this article we report the synthesis of quinoxaline derivatives in the presence of ibx. 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. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. Synthesis and antimicrobial activity of some new substituted quinoxalines. Synthesis, reactions and biological activity of quinoxaline derivatives. Efficient and practical protocol for the synthesis of pyridopyrazines. The solventfree synthesis of quinoxalines using the sulfonic acid. Molecules free fulltext synthesis and antimicrobial activity of. Efficient synthesis of quinoxaline derivatives catalyzed by p. 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.
Pdf green chemistry approaches for the synthesis of. Quinoxalinediones are a family of related compounds sharing the same bicyclic core. This method had many dramatic advantages, such as the short reaction time 26 min, high yields 7198%, and. Photochemistry department heterocyclic unit, national research centre, giza, egypt. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on. Twentynine new 67substituted quinoxaline 2carboxylate 1,4dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. Molecules 2019, 24, 1175 3 of 22 is a wellknown diarylurea multitargeted inhibitor of several kinases including raf, vegfr, ckit and pdgfr 17. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman. This involves the generation of furo3,4bpyrazine and furo3,4b quinoxaline as transient intermediates, which were trapped with dielsalder dienophiles.
Progress in quinoxaline synthesis part 2 request pdf. Benzil quinoxaline synthesis cameron trefny jason young tth 5. A greener chemistry approach for synthesis of 2,3diphenyl. Quinoxalines and fused ring systems show diverse pharmacological activities.
Molecules free fulltext synthesis and evaluation of new. The most potent compound among the series is analog 25 with ic50 value 3. 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. Synthesis of quinoxaline derivatives using sulfonic acid. The quinoxaline moiety is present in a large variety of physiologically active compounds, with applications varying from medicinal to agricultural. Chromophorelabeled quinoxaline derivatives as efficient. Environeconomic synthesis and characterization of some new 1,2,4triazole derivatives as organic fluorescent materials and potent fungicidal agents. The method shows high yields of quinoxaline derivatives under heterogeneous conditions. Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2dicarbonyl compounds in the presence of ibx in acetic acid. Quinoxaline, benzopyrazine, antimicrobial activity introduction quinoxalines, also called a benzopyrazines, in organic chemistry, it is a hetrocyclic compounds. 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. 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 a mancude organic heterobicyclic parent, an orthofused heteroarene and a naphthyridine.
The most common approach for the preparation of quinoxalines involves the. The regioselectivity in their dielsalder cycloaddition reactions. Compared with the classical synthetic method, this new method has the advantages of convenient manipulation and environmental friendliness. 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. Zhou jf, gong gx, shi kb, zhi sj 2009 catalyst free and solvent free method for the synthesis of quinoxalines under microwave irradiation. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. Conventionally, quinoxaline synthesis can be achieved by the reaction of 1. 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. The reactions were carried out under catalyst free, solvent free, and microwaveirradiation conditions, affording the corresponding quinoxalines. We have synthesized quinoxaline analogs 125, characterized by 1hnmr and hreims and evaluated for thymidine phosphorylase inhibition. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline. Under the rhiii catalyst, reaction proceeded through the free amine assisted c2. Spectrophotometric study of coii and niii complexes with quinoxaline 2,3dithiol has been reported by ayres et al 23. A convenient process of preparing of 2,3 diphenyl quinoxaline derivatives.
The solvent free synthesis of quinoxalines using the sulfonic acid functionalized imidazolium salts. Synthesis of quinoxalines promoted by ecofriendly nanokaoline. Lproline as an e cient organocatalyst for the synthesis of quinoxaline derivatives under solvent free conditions a. Ionic liquid 1butyl3methylimidazolium bromide bmimbr. In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. Efficient synthesis of quinoxaline derivatives catalyzed. Design and synthesis of new quinoxaline derivatives as. Synthesis of quinoxaline quinones and regioselectivity in. The procedure worked well for a variety of starting materials and the corresponding products were obtained. 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. Ch 2extrusion under metal free conditions features high regioselectivity, efficiency, and environmental friendliness. The synthesis and chemistry of quinoxalines have attracted considerable attention in the past 10 years. Lproline as an e cient organocatalyst for the synthesis.
Comparison of ethanol and water in the presence of the reusable catalyst cellulose sulfuric acid. A simple and efficient protocol for the synthesis of quinoxalines. Chemistry department, faculty of science, jazan university, saudi arabia. It is rare in natural state, but their synthesis is easy to perform. 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. Abstract a green and efficient procedure for the synthesis of quinoxalines is reported starting from benzil and 1,2diaminobenzene. Onepot threecomponent synthesis of quinoxaline and. The quinoxaline synthesis involving the reaction of substituted. Highly efficient synthesis of quinoxaline derivatives from 1,2benzenediamine and. The classical synthesis of quinoxaline derivatives involves the double condensation of aryl 1,2diamines with 1,2.
Quinoxaline is a naphthyridine in which the nitrogens are at positions 1 and 4. A novel and efficient procedure was introduced for the synthesis of alkyl acetates bearing arylthio and quinoxaline moieties from the reaction of o. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. H activation followed by amidation leading to the diazepino1,7. Facile method of quinoxaline synthesis using phenol as a new, efficient and cheap catalyst at room temperature.
They can be formed by condensing orthodiamines with 1,2diketones. The reaction proceeds very cleanly at room temperature in a onepot procedure and free of side products. An efficient catalystfree protocol for the synthesis of quinoxaline. Pdf on apr 9, 2019, ankush mishra and others published a catalystfree expeditious green synthesis of quinoxaline, oxazine, thiazine. Microwaveassisted catalystfree and solventfree method. Pdf facile method of quinoxaline synthesis using phenol. 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. Wong and coworkers have studied quinoxaline derivatives theoretically12.
Quinoxalinedione is an organic compound with the formula c 6 h 4 nh 2 co 2. Pdf a convenient process of preparing of 2,3 diphenyl. Synthesis of quinoxaline derivatives over highly efficient and reusable bronsted acidic ionic liquids. A greener chemistry approach for synthesis of 2,3diphenyl quinoxaline. A series of new quinoxaline derivatives of dehydroabietic acid daa were designed and synthesized as potential antitumor agents. An efficient protocol for the synthesis of quinoxaline. Pdf a simple, highly efficient and green procedure for the preparation of quinoxaline in the. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the. Quinoxaline derivative an overview sciencedirect topics. In this laboratory experience you will examine the synthesis of heterocyclic molecules. Facile synthesis of quinoxaline derivatives using o. An efficient synthesis of quinoxaline derivatives catalyzed by ptoluene sulfonic acid under solventfree conditions was reported by shi and dou 86 scheme.
The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2diaminobenzene. 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. Numerous methods are available for the synthesis of quinoxaline derivatives which. Highly efficient synthesis of quinoxaline derivatives from. 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. In specific you are using a safe substance thiamine, vitamin b1 as a catalyst. The cdk15 inhibitor, also referenced under cas 40254908, controls the biological activity of cdk15. It is a colorless solid that is soluble in polar organic solvents. 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. Pdf a catalystfree expeditious green synthesis of quinoxaline. Synthesis and antimicrobial activities of some novel. View notes ch 11 benzil quinoxaline synthesis report from chem 255 at ohio state university. Quinoxaline article about quinoxaline by the free dictionary. A facile synthesis of quinoxaline quinones is reported.
Synthesis of new quinoxaline2carboxylate 1,4dioxide. Farrokhinia department of chemistry, faculty of sciences, central tehran branch, islamic azad university, tehran, iran. An efficient catalystfree protocol for the synthesis of quinoxaline derivatives under. Cancer, drug discovery, synthesis, quinoxaline, heterocyclic compounds, biological activity.
Green chemistry approaches for the synthesis of quinoxaline derivatives. Ecofriendly approach to access of quinoxaline derivatives. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. 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. An efficient protocol for the synthesis of quinoxaline derivatives at. Consequently, a large variety of synthetic methods for the synthesis of functionalized quinoxalines have been reported in literature. Among the series, nineteen analogs showed better inhibition when compared with the standard inhibitor 7deazaxanthine ic50 38. A convenient synthesis of substituted quinoxalines in good yields from ophenylenediamines and ynones via michael addition, dehydration condensation, and basepromoted c. A green protocol for the synthesis of quinoxaline derivatives catalyzed by polymer supported sulphanilic acid.
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