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Heterocyclization of derivatives of thioncarboxylic acids to 1,3,4-thiadiazoles under the action of tert-butyl hypochlorite

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

A method for synthesis of 2-alkyl-5-aryl- and 2,5-diaryl-1,3,4-thiadiazoles by successive reaction of thioamides with tert-butyl hypochlorite and benzothiohydrazides was developed. The first step in the formation of 1,3,4-thiadiazoles consists of oxidation of thioamides with tert-butyl hypochlorite with O atom transfer to the S atom, which was established by transformation of N-methyl-thiobutanamide into N-(methylimino)butanesulfenic acid.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    D. V. Demchuk, A. I. Lutsenko, É. I. Troyanskii & G. I. Nikishin

Authors
  1. D. V. Demchuk
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  2. A. I. Lutsenko
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  3. É. I. Troyanskii
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  4. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1843–1848, August, 1989.

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Demchuk, D.V., Lutsenko, A.I., Troyanskii, É.I. et al. Heterocyclization of derivatives of thioncarboxylic acids to 1,3,4-thiadiazoles under the action of tert-butyl hypochlorite. Russ Chem Bull 38, 1690–1695 (1989). https://doi.org/10.1007/BF00956957

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  • DOI: https://doi.org/10.1007/BF00956957

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