DERIVATIVES OF 4-AMINO-4H-1,2,4-TRIAZOLE-3-THIOLS LINKED TO PYRROLE CYCLE AND SOME PRODUCTS OF THEIR S-ALKYLATION

Authors

  • A. T. Bijev University of Chemical Technology and Metallurgy Department of Organic Synthesis and Fuels 1756 Sofia
  • P. Prodanova University of Chemical Technology and Metallurgy Department of Organic Synthesis and Fuels 1756 Sofia

DOI:

https://doi.org/10.1007/7641

Keywords:

pyrroles, 4H-1, 2, 4-triazole, alkylation, cyclization

Abstract

The study offers an access to 21 new heterocyclic compounds representing pyrrole derivatives of 4-amino-4H-1,2,4-triazole-3-thiols or 1,3,4-oxadiazole-2-thiols. The principal synthetic approach is based on the cyclization of substituted potassium 2-(pyrrolecarbonyl)hydrazine-1-carbodithionate with hydrazine hydrate to 5-(substituted pyrrolyl)-4-amino-4H-1,2,4-triazole-3-thiols, followed by S-alkylation with methyl iodide or benzyl chloride. Among the resulted thirteen S-alkyl derivatives, five 1,3,4-oxadiazole derivatives have been isolated as secondary products and their formation is explained as a result of S-alkylation of intermediate 1,3,4-oxa- diazole-2-thiols, generated in the alkaline medium.

How to Cite
Bijev, A. T.; Prodanova, P. Chem. Heterocycl. Compd. 2007, 43, 306. [Khim. Geterotsikl. Soedin. 2007, 383.]

For this article in the English edition see DOI 10.1007/s10593-007-0046-5

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Published

2023-03-30

Issue

No. 3 (2007)

Section

Original Papers