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

Authors

  • Mohamed Abass Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo
  • Hany M. Hassanin Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo
  • Hassan A. Allimony Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo
  • Heba Hassan Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo

DOI:

https://doi.org/10.1007/2575

Keywords:

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

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

Author Biographies

Mohamed Abass, Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo

Department of Chemistry

Hany M. Hassanin, Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo

Department of Chemistry

Hassan A. Allimony, Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo

Department of Chemistry

Heba Hassan, Department of Chemistry, Faculty of Education, Ain Shams University, Heliopolis 11757, Cairo

Department of Chemistry

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Published

2015-12-28

Issue

Vol. 51 No. 11/12 (2015)

Section

Original Papers