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Pyrazolo[4?,3?:5,6]pyrano[2,3-b]quinoxalin-4(1H)-one: Synthesis and characterization of a novel tetracyclic ring system

(Chemical Equation Presented) Derivatives of the hitherto unknown ring system, pyrazolo[4?,3?:5,6]pyrano[2,3-b]quinoxalin-4(1H)-one, are synthesized in one step from the corresponding 1-substuituted or 1,3-disubstituted 2-pyrazolin-5-ones and 3-chloroquinoxaline-2-carbonyl chloride using calcium hydroxide in boiling 1,4-dioxane. The parent system carrying no substituent in positions 1 and 3 is obtained upon treatment of the 1-PMB (p-methoxybenzyl) protected congener with trifluoroacetic acid. Detailed NMR spectroscopic investigations including unambiguous chemical shift assignments of all 1H, 13C, and 15N resonances of the obtained tetracycles are reported.

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Quinoxaline | C8H6N1021 | ChemSpider

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Static and Dynamic Properties of Quinoxalines in the Phosphorescent Triplet State from Optically Detected Magnetic Resonance

The static and dynamic properties of the phosphorescent triplet states of quinoxaline and 2,3-disubstituted derivatives in hexane have been studied at 1.4 K using the methods of optically detected magnetic resonance.In addition, the absorption and phosphorescence excitation spectra have also been measured to attain the information about the low lying excited states.A systematic comparison has been made for the purpose of examining the effect of substitution.A significant enhancement of the pumping rates for the y spin sublevel observed in the chlorine-substituted derivatives is concluded to be due to the additional indirect process of intersystem crossing which occurs from S1 of n,?* to T1 passing through the intermediate triplet state of ?,?*.A detailed discussion on the observed phosphorescence spectra originating from the three sublevels has achieved a satisfactory success in understanding the mechanisms responsible for the radiative decay processes.It is concluded that the mechanisms due to vibronic coupling with closely lying n,?* triplet states are of little importance in the systems studied here.

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Quinoxaline | C8H6N1048 | ChemSpider

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Synthesis and reactivity of pyrrolo[1,2-a]quinoxalines. Crystal structure and AM1 calculation

2-Methylquinoxaline reacts with ethyl bromopyruvate giving 2-substituted pyrrolo[1,2-a]quinoxalines. The yield of the condensation depends on the functionalization of starting materials, and optimization is obtained with 2-dimethylamino-3-methylquinoxaline (1c). Reactivity of the resulting pyrrolo[1,2-a]quinoxalines was investigated and supported by a theoretical approach (AM1 calculation performed with the MOPAC 6.0 software). X-ray analysis of 5 which crystallizes in the monoclinic system, space group P21/n, with a = 9.095(1), b = 8.972(1), c = 17.749(3) A, beta = 96.56(1), is also reported.

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Quinoxaline | C8H6N1013 | ChemSpider

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Synthesis and antidiabetic activity of 3,6,7-trisubstituted-2-(1H-imidazol- 2-ylsulfanyl)quinoxalines and quinoxalin-2-yl isothioureas

Two series of 3,6,7-trisubstituted-2-(1H-imidazol-2-ylsulfanyl)- quinoxalines 2a-1 and 2-(quinoxalin-2-yl)-isothioureas 3a-1 were prepared. All the test compounds 2a-1 and 3a-1 were screened in vitro, in a RIN5F cell-based assay for glucose-dependent insulinotropic activity. A significant concentration and glucose-dependent insulin secretion effect was seen with compounds 2a-1 and the insulinotropic activity of compound 21 was found to be identical to that of the standard compound (6,7-dichloro-2-trifluromethyl-3-(5-methyl-1,3,4- thiadiazo-2-ylsulfanyl)-quinoxaline (1)).

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Synthesis and anti microbial activity of quinoxaline based thiazolidinones and azetidinones

Several 2-aryl-3- (3?methyl quinoxalin-2?-yl-amino) 4-thiazolidinoes 6a-l and 1-N-(3?methylquinoxalin-2?-yl-amino)4-aryl -3-chlodro-2-azetidinones 7a-l have been synthesized and tested for their antimicrobial and antifungal activity against different microorganism. The structure of compounds 6a-l and 7a-l have been conformed on the basis of their elemental and spectral data.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1050 | ChemSpider

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Synthesis of Condensed Quinoxalines. VI. Synthesis of 1H-Pyrazolo<3,4-b>quinoxaline N-Oxides and Related Compounds

Oxidation of 1H-pyrazolo<3,4-b>quinoxalines (1a: R=H, 1b: R=CH3) with m-chloroperbenzoic acid (MCPBA) gave the 4-oxides (2a, b).The structures of 2a, b were confirmed by synthesis, by condensing 2-chloroquinoxaline-3-carbaldehyde 4-oxide (6) with appropriate hydrazines.Further oxidation of 2a with MCPBA gave the 4,9-dioxide (8).Treatment of 1,2-dihydro-2-oxoquinoxaline-3-carboxamide (10) and 1,2-dihydro-2-oxoquinoxaline-3-carbonitrile 4-oxide (13) with a mixture of POCl3 and PCl5 or POCl3-dimethylformamide afforded 2-chloroquinoaline-3-carbonitrile (11) and its 4-oxide (14), respectively.When 11 and 14 were reacted with hydrazines, the correponding 3-amino-1H-pyrazolo<3,4-b>-quinoxalines (12a, b) and their 4-oxides (15a, b) were obtained in high yields.The reaction of ethyl 2-chloroquinoxaline-3-carboxylate (16) with hydrazine hydrate afforded a mixture of uncyclized products, N,N’-bis(2-ethoxycarbonyl-3-quinoxalinyl)hydrazine (17), ethyl 2-hydrazinoquinoxaline-3-carboxylate (18) and 2-hydrazinoquinoxaline-3-carbohydrazide (19).Keywords 1H-pyrazolo<3,4-b>quinoxaline 4-oxide; 1H-pyrazolo<3,4-b>quinoxaline 4,9-dioxide; 3-amino-1H-pyrazolo<3,4-b>quinoxaline 4-oxide; 2-chloroquinoxaline-3-carbaldehyde 4-oxide; hydrazine; N,N’-bis(2-ethoxycarbonyl-3-quinoxalinyl)hydrazine; ethyl 2-hydrazinoquinoxaline-3-carboxylate; 2-hydrazinoquinoxaline-3-carbohydrazide

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1054 | ChemSpider

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Synthesis and antimicrobial activity of some new quinoxaline derivatives

Quinoxaline derivatives have several pharmaceutical applications. Quinoxaline derivatives are benzoheterocycles, quinoxalin-2-ones and quinoxaline-2, 3-diones. Some of quinoxaline compounds are synthesized and characterized such as 8-bromo-2-methoxyquinoxaline, tert-butyl 1-(2-methoxyquinoxalin-8-yl) pyrrolidin-3-ylcarbamate, tertbutyl (R)-1-(2-methoxyquinoxalin-8-yl) pyrrolidin-3-ylcarbamate, tert-butyl (S)-1-(2-methoxyquinoxalin-8-yl)pyrrolidin-3-ylcarbamate, 1-(2-methoxyquinoxalin-8-yl) pyrrolidin-3-amine, (R)-1-(2-methoxyquinoxalin-8-yl)pyrrolidin-3-amine, (S)-1-(2-methoxyquinoxalin-8-yl)pyrrolidin-3-amine. Biological activity results were statisfactory.

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Quinoxaline | C8H6N1047 | ChemSpider

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Solvent free microwave accelerated synthesis of heterocyclic thiazolidin-4-ones as antimicrobial and antifungal agents

A simple and efficient method has been developed for conversion of arenecarbaldehyde-3-methylquinoxalin-2-ylhydrazones to 3-(2-methylquinoxalin-3- yl)-2-(substitutedphenyl)thiazolidin-4-ones in good yields using microwave irradiation technique on silica as solid support under solvent free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, 1H NMR, and mass spectroscopy. All the synthesized thiazolidinones were investigated for their antimicrobial and antifungal activities. The results of the biological activities revealed that the compounds 3b, 3d, 3f and 3h exhibited excellent antibacterial activities while 3d and 3h exhibited good antifungal activity.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N1044 | ChemSpider

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Alkynyl- and Dialkynyl-quinoxalines. Synthesis of Condensed Quinoxalines

Condensation of 2-chloro- and 2,3-dichloroquinoxalines with alk-1-ynes in the presence of bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide gives mono- and di-alkynylquinoxalines.Addition of amines to these products gives stable enamines; hydration gives 2′-oxoalkyl compounds which exist predominantly in the intramolecularly hydrogen-bonded enol form.Condensation of the alkynylquinoxalines with diethyl sodiomalonate, and related compounds, yields pyrido<1,2-a>quinoxalin-4-one derivatives. 2-Alkynyl-3-chloroquinoxalines are intermediates for convenient syntheses of pyrrolo<2,3-b>quinoxalines.

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Quinoxaline | C8H6N1009 | ChemSpider

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A FACILE SYNTHESIS OF NOVEL TRICYCLIC COMPOUNDS, TETRAZOLOQUINOXALINES AND 1,2,4-TRIAZOLOQUINOXALINES

Novel 5-methyltetrazolo<1,5-a>quinoxalin-4-ones (5) and 5-methyl-1,2,4-triazolo<4,3-a>quinoxalin-4-ones (7) could be synthesized from 1-methyl-3-chloroquinoxalin-2-ones (3) and 1-methyl-3-hydrazinoquinoxalin-2-ones (6), respectively.Further extensive study was carried out to synthesize 4- or 7- substituted and 4,7-disubstituted tetrazolo<1,5-a>quinoxalines (10) and 1,2,4-triazolo<4,3-a>quinoxalines (12).

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