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SUBSTITUTED QUINOLINONES. 27. REGIOSELECTIVE SYNTHESIS OF PYRAZOLO-, OXAZOLO-, AND TRIAZEPINOQUINOLINE DERIVATIVES

Mohamed Abass, Hany M. Hassanin, Hassan A. Allimony, Heba Hassan
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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.

How to Cite
Abass, M.; Hassanin, H. M.; Allimony, H. A.; Hassan, H. Chem. Heterocycl. Compd. 2015, 51, 1023. [Khim. Geterotsikl. Soedin. 2015, 51, 1023.]

For this article in the English edition see DOI 10.1007/s10593-016-1813-y


Keywords


quinolinone; Beckmann rearrangement; heterocyclic synthesis; nucleophilic condensation; regioselective cyclization

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