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Substituted quinolinones 27.* Regioselective synthesis of pyrazolo-, oxazolo-, and triazepinoquinoline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis, 11757, Cairo, Egypt

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

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  1. Mohamed Abass
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  2. Hany M. Hassanin
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  3. Hassan A. Allimony
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  4. Heba Hassan
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Correspondence to Heba Hassan.

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* For Communication 26, see1.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(11/12), 1023–1029

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Abass, M., Hassanin, H.M., Allimony, H.A. et al. Substituted quinolinones 27.* Regioselective synthesis of pyrazolo-, oxazolo-, and triazepinoquinoline derivatives. Chem Heterocycl Comp 51, 1023–1029 (2015). https://doi.org/10.1007/s10593-016-1813-y

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  • DOI: https://doi.org/10.1007/s10593-016-1813-y

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