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The cyanoethylation reaction and electronic structure of N-phenylated thioamides of the 1,2,4-triazole and tetrazole series

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cyanoethylation reactions of 1-phenyl-1,2,4-triazoline-3-thione (I) and of 1-phenyl-1,2,4,-triazoline-5-thione (II) have been studied. The cyanoethylation of I forms only S-cyanoethyl derivates,and the cyanoethylation of II only N-cyanoethyl derivatives. The structures of the reaction products were confirmed by UV spectroscopy and by independent synthesis. On the basis of a quantum-mechanical analysis of the compounds, their tautomeric forms, and the assumed primary reaction products, it has been concluded that the mechanism of the cyanoethylation and transcyanoethylation reactions of these heterocyclic thioamides is a common one.

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Authors and Affiliations

  1. Kirov Urals Polytechnic Institute, Sverdlovsk

    E. G. Kovalev & I. Ya. Postovskii

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  1. E. G. Kovalev
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  2. I. Ya. Postovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1138–1144, August, 1970.

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Kovalev, E.G., Postovskii, I.Y. The cyanoethylation reaction and electronic structure of N-phenylated thioamides of the 1,2,4-triazole and tetrazole series. Chem Heterocycl Compd 6, 1064–1069 (1970). https://doi.org/10.1007/BF00480652

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  • DOI: https://doi.org/10.1007/BF00480652

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