Substituted Quinolinones. Part 27. Regioselective Heterocyclization of Some Diazolo- and/or Triazepino[b or c]quinoline Derivatives

Mohamed Abass; Hany Hassanin; hassan Allimony; heba hassan

doi:10.3390/ecsoc-19-a018

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Substituted Quinolinones. Part 27. Regioselective Heterocyclization of Some Diazolo- and/or Triazepino[b or c]quinoline Derivatives

¹ Department of Chemistry, Faculty of Education, Ain Shams University

Published: 30 October 2015 by MDPI in The 19th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-19-a018

Abstract:

Reactivity of 3-acetyl-4-methylthioquinolin-2(1H)-one (1) towards 1,2- and/or 1,4-diazanucleophiles has been studied under different reaction conditions. Condensation of key compound 1 with hydrazine, phenylhydrazine, hydroxylamine hydrochloride, semicarbazide and thiosemicarbazide was carried out in different media. It was found that the nature of products is extremely dependent on both reactivity of the reagent and the ambient conditions. Accordingly, the reaction regioselectivety led to different [1,2]diazolo and or [1,2,4]triazepino[b or c]quinoline derivatives in addition to open chain condensates which were transformed to either annellated heterocyclo[b or c] quinolines, in good yields. The structure of new products was established on basis of their analytical and spectral data.

Keywords: Quinolinone, Heterocyclic synthesis, Nucleophilic condensation, Regioselective cyclization, Beckman rearrangement.

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Comments on this paper

Mohamed Abass

1 November 2015

Congratulations for publication of your PhD first paper

congratulations Ms Heba. The edition style is very well. Please let full manuscript be available for request to whom interests in this paper. Good luck and waiting for useful discussion about this article.

Heba Hassan

1 November 2015

Thanks, my professor for ever.