M. Abass, Hany M Hassanin, H. A. Allimony
Dec 28, 2015
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Influential Citations
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Journal
Chemistry of Heterocyclic Compounds
Abstract
Reactivity of 3-acetyl-4-(methylsulfanyl)quinolin-2(1H)-one towards 1,2- and/or 1,4-diazanucleophiles has been studied under different reaction conditions. Condensation of 3-acetyl-4-(methylsulfanyl)quinolin-2(1H)-one with hydrazine, phenylhydrazine, hydroxylamine hydrochloride, semicarbazide, and thiosemicarbazide was carried out in different media. The structure of the reaction products was dependent not only on the reagent used, but also on the solvent and reaction temperature. Accordingly, the reaction regioselectively produced in good yields pyrazolo[3,4-b]quinoline, pyrazolo[4,3-c]quinoline, oxazolo[5,4-b]quinoline, oxazolo[4,5-c]quinoline, isoxazolo-[4,5-c]quinoline, [1, 2, 4]triazepino[5,6-b]quinoline, and [1,2,4]triazepino[6,5-c]quinoline derivatives in addition to open-chain condensates which, too, were transformed to the respective cyclic products. The structures of new products were established on basis of their analytical and spectral data.