Spectrophotometric study of coii and niii complexes with quinoxaline 2,3dithiol has been reported by ayres et al 23. Quinoxalines and fused ring systems show diverse pharmacological activities. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2diaminobenzene. A convenient and efficient synthesis of new bis quinoxaline is described, involving condensation of 1,2diamines with 9ethyl3,6di1,2dioxoethylcarbazole in the presence of tonsil clay, a readily available and inexpensive catalyst. Sigmaaldrich offers a number of quinoxaline products. Cshaped diastereomers containing cofacial thiophene. Furthermore, the quinoxaline ring is a core structure of several drug molecules and acceptors such as clofazimine, echinomycin and actinomycin 1417. Synthesis and characterization of two diastereomeric cshaped molecules containing cofacial thiophenesubstituted quinoxaline rings are described. Sulfonamides and quinoxaline derivatives possess many types of biological activities and have been recently reported to show substantial antitumor activity. Synthesis, characterization, antibacterial and antifungal activities of new quinoxaline 1,4dinoxide derivatives abstract fulltext html download as pdf size. Quinoxalines synthesis, reactions, mechanisms and structure.
A practical efficient and rapid synthesis of new quinoxalines catalyzed by citric acid as a trifunctional bronsted acid at room temperature under green condition sami sajjadifar1, mohammad ali zolfigol2, gholamabbas chehardoli3, sara miri1, parvin moosavi1,2 1department of chemistry, payame noor university, po box 193954697. Quinoxaline derivatives are an important class of heterocycle compounds, where n replaces some carbon atoms in the ring of naphthalene. A quinoxaline derivative as a potent chemotherapeutic. They are potential ntype small molecules, capable of undergoing successive reductions and selfassembling in facetoface. These catalysts were prepared by incipient wetness impregnation. Pdf convenient methods for the synthesis of quinoxaline derivatives with the use of nucleophilic aromatic substitution of hydrogen in heteroaromatic. Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. 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. Onepot threecomponent synthesis of quinoxaline and. It is a photocatalyst in photopolymerization and photoinitiator.
Synthesis of novel quinoxaline carboxylic acid derivatives. Quinoxaline, benzopyrazine, antimicrobial activity introduction quinoxalines, also called a benzopyrazines, in organic chemistry, it is a hetrocyclic compounds. The method shows high yields of quinoxaline derivatives under. Recently, we have also reported some quinoxalinebased colorimetric and ratiometric sensors for specific detection of nickel cations 1820. 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. Sensing study of quinoxaline analogues with theoretical. Pdf a simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2chloro quinoxaline. 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 number of synthetic methods are available for the synthesis of 1 and its derivatives. Pdf new opportunities for the synthesis of quinoxaline. Onepot threecomponent synthesis of quinoxaline and phenazine ring systems using fischer carbene complexes priyabrata roy and binay krishna ghorai beilstein j. Dimethyl sulfoxide involved onepot synthesis of quinoxaline.
The catalyst is recyclable and reusable 2006 published by elsevier b. Their structures were confirmed by using 1 h nmr, ir, and mass analysis. Photochemistry department heterocyclic unit, national research centre, giza, egypt. Various 6aralkyl9substituted6hindolo2,3bquinoxalines were synthesized by reaction of 1,5disubstituted 2,3dioxo2,3dihydroindole with orthophenylene diamine. Synthesis and influence of two quinoxalinone derivatives. Application of a reusable cobased nanocatalyst in alcohol. A convenient process of preparing of 2,3 diphenyl quinoxaline derivatives. The synthesis of quinoxalines has been intensively studied in the past, especially because of the diverse biological activities ascribed to many representatives of this. Additionally, the quinoxaline moieties of 1ah2 and 1bh2 act as electronwithdrawing groups, introducing lower. Synthesis and evaluation of quinoxaline derivatives as potential. Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 43substitutedthioureidonquinoxalin2ylbenzenesulfonamide derivatives. Novel quinoxaline 1,4dinoxide derivatives as new potential antichagasic agents enrique torresa, elsa morenoviguriab.
Compounds 3a3i were obtained by the condensation of ophenylenediamines with 1,2. Similar chemistry was applied by heeg and coworkers in their synthesis of substituted quinoxalines 244, which were. In the light of these facts we decided to synthesize some new quinoxaline derivatives incorporating aromatic aldehyde and aromatic amine moieties attached to a 2hydroxy3methylquinoxaline nucleus with an ether linkage followed by the. The synthesis of the new derivatives was optimized through the use of a new and more efficient microwaveassisted organic synthetic method.
Many researchers have reported the synthesis and biological activity of quinoxaline derivatives 11,12,14. 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 evaluation of thermooxidative properties of a series of benzimidazole copolymers by defense technical information center. The quinoxaline nucleus is one of the most important heterocyclic scaffolds. A library of quinoxaline derivatives were prepared to target. Then reaction mixture was cooled and poured into water to get sulfonamide derivative of 2, 3diphenylquinoxaline. Facile method of quinoxaline synthesis using phenol as a new. 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. For more information, read michigan publishings access and usage policy. Synthesis of bisquinoxaline derivatives using tonsil clay. Preparation, structures and preliminary hostguest studies of fluorinated synbisquinoxaline molecular tweezers markus etzkorn, jacob c. N n quinoxaline o o ch3 ch3 butane2,3dione nh2 nh2 benzene1,2diamine scheme 1.
Appreciable anticancer activity of compounds 5b, 5d, 5g and 5l at various cell lines among 59 human tumor cell panels was observed. 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. Quinoxaline antibiotic is a generic name given to a family of heterodetic cyclodepsipeptide antibiotics which contain a quinoxaline moiety in the molecule kuroya et al. It is a colorless oil that melts just above room temperature. Synthesis and biological activity of new quinoxaline. Biological activities of quinoxaline derivatives a antitubercular activity. Synthesis, anticancer and cytostatic activity of some 6hindolo2,3bquinoxalines. Benzil quinoxaline synthesis cameron trefny jason young tth 5.
Natural products containing quinoxaline ring are rare and can be easily prepared or synthesized. Pdf the objective of present research work is to provide green technique for synthesis of 2,3diphenyl quinoxaline. Synthesis of bisquinoxaline derivatives using tonsil clay as. Synthesis of new quinoxaline derivatives springerlink. The development of an expedient synthesis toward quinoxaline ringembedded polyacenoquinone esters with the generic structure a is demonstrated by the synthesis of penta and hexacenoquinone esters. 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. Synthesis, anticancer and cytostatic activity of some 6h. This work is licensed under a creative commons attributionnoncommercial 3. It is the raw material for synthesis of benzil by organic oxidation with nitric acid or oxone. Synthesis and antimicrobial activities of some novel. Thermooxidation studies of the quinoxaline system and certain benzimidazole copolymer systems. Synthesis, characterization and protonation behavior of. View notes ch 11 benzil quinoxaline synthesis report from chem 255 at ohio state university.
Sequential reactions of ophenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. Introduction quinoxaline derivatives are a very important class of nitrogencontaining compounds and have been widely used in dyes1,pharmaceuticals2 and electricalphotochemical materials3. Synthesis and activity of some quinoxaline analogues of streptonigrin. Quinoxaline2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. An international journal for rapid communication of synthetic organic chemistry. The pdf file you selected should load here if your web. Chemistry department, faculty of science, jazan university, saudi arabia. Synthesis, reactions and biological activity of quinoxaline. Pdf design and synthesis of some new quinoxalinebased. Quinoxaline itself prepared by the condensation of ophenylene diamine with glyoxal sodium bisulphite in 8590% yield29. Synthesis, characterization, antibacterial and anti. Very recently we have developed a convenient and efficient procedure for synthesis of quinoxaline derivatives using cupric sulfate pentahydrate as catalyst. Synthesis of highly functionalized polycyclic quinoxaline.
We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts. Quinoxaline 2carboxaldehyde was also used for the synthesis of a large number of new condensed quinoxalines and heteroaryl quinoxalines. Preparation, structures and preliminary hostguest studies. Synthesis, reactions and biological activity of quinoxaline derivatives.
Proceeding from 2aminoquinoxaline3carbonitrile 1,4dioxides new derivatives of quinoxaline and quinoxaline 1,4dioxide were synthesized containing in the position 3 of the quinoxaline fragment 1,2,4oxadiazole and tetrazole rings. Onepot and efficient protocol for synthesis of quinoxaline. Exploring biological activities of quinoxaline derivatives. 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. Facile method of quinoxaline synthesis using phenol as a. Its molecular formula is c 8 h 6 n 2, formed by the fusion of two aromatic rings, benzene and pyrazine. In addition, the synthesis of two new 1,4benzodiazine derivatives and the catalytic activity of magnesium sulfate heptahydrate. Ecofriendly approach to access of quinoxaline derivatives. The quinoxaline synthesis was performed in ethanol as a green and suitable solvent at ambient temperature to afford the. Quinoxalines synthesis, bronsted acidic ionic liquids bails, green chemistry. Synthesis of nheterocycles benzofused nheterocycles synthesis of quinoxalines.
It is rare in natural state, but their synthesis is easy to perform. Synthesis and neuropharmacological evaluation of some. A multicomponent synthesis of substituted 3styryl1hquinoxalin2ones is described. 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. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol. Convenient and simple procedures for the synthesis of phenazine and quinoxaline derivatives were developed via a reaction of ophenylenediamines and 1,2dicarbonyl compounds.
Pdf a convenient process of preparing of 2,3 diphenyl. Moreover, applying the transfer hydrogenation and acceptorless. 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. Initial studies on the mechanism of thermooxidation of the quinoxaline system.
Quinoxalines exist in several different biologically active compounds. Therefore, the aim of this project was to synthesis some novel of 2,3substituted quinoxaline. This is a pdf file of an unedited manuscript that has been. The most common method is condensation of an aryl 1,2diamine with 1,2dicarbonyl compound in suitable solvent 19, 20 scheme1. Although quinoxaline itself is mainly of academic interest, quinoxaline. The first four chapters present a survey of the developments in quinoxaline chemistry since the publication of the monograph on condensed pyrazines by cheeseman.
It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Therefore, the aim of this project was to synthesis some novel of 2,3substitutedquinoxaline. Quinoxaline derivative an overview sciencedirect topics. They can be formed by condensing orthodiamines with 1,2diketones. Detailed experimental procedure and 1h and c nmr spectra of all compounds pdf. Xushuang han, xuan liu and chen ma, dimethyl sulfoxide involved onepot synthesis of quinoxaline derivatives, the journal of organic chemistry, 10. The catalytic test was performed under different reaction conditions in order to know the performance of the synthesized catalysts. A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. These colorless antibiotics are derived from various species of streptomycetes and are highly active against grampositive bacteria. 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. Consequently, a large variety of synthetic methods for the synthesis of functionalized quinoxalines have been reported in literature. Synthesis of ethyl 3amino1,4dihydroquinoxaline2carboxylate 2. Condensed quinoxalines were obtained by oxidative cyclisation of quinoxaline 2carboxaldehyde hydrazone and phenylhydrazone using lead tetraacetate. Mar 12, 2012 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.
An efficient protocol for the synthesis of quinoxaline. This document was downloaded for personal use only. Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible. Synthesis of novel quinoxaline carboxylic acid derivatives for antimicrobial investigation m s a elgaby, m m f ismail b, y a ammarc. Ahmedy, synthesis of some quinoxaline derivatives containing indoline2,3dione or thiazolidine residue as potential antimicrobial agents, archives of pharmacal research, vol. Facile synthesis of quinoxaline derivatives using o. Pdf green synthesis of quinoxaline derivatives researchgate. A facile synthesis of phenazine and quinoxaline derivatives. The quinoxaline derivative 3b, with high affinity and selectivity for tau aggregates, favorable fluorescence turnon capability and brain kinetics, was successfully applied to the detection of tau tangles both in vitro and in. Quinoxaline2, 3dione obtained from cyclocondensation reaction of ophenylene diamine with oxalic acid was reacted with three different ketones and formaldehyde to give the corresponding mannich bases in satisfactory yield. New quinoxaline derivatives were prepared by the reaction of 2 hydroxyquinoxaline 1. Syntheses of quinoxaline derivatives via many different methods of synthetic strategies have been presented. Synthesis of bisquinoxaline derivatives using tonsil clay as a catalyst. Files available from the acs website may be downloaded for.