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Heterocyclic Communications

Editor-in-Chief: Strekowski, Lucjan

Ed. by Baumstark, Alfons L. / Murata, Shizuaki / Saczewski, Jaroslaw / Stephens, Chad

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Synthesis of 3-alkyl-5-allylamino-2-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement

Maksym Fizer1 / 1 / Vjacheslav Baumer2 / Vasil Lendel1

1Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod 88000, Ukraine

2SSI “Institute for Single Crystals” NASU, Lenina ave. 60, Kharkiv 61001, Ukraine

Corresponding author: Mikhailo Slivka, Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod 88000, Ukraine

Citation Information: Heterocyclic Communications. Volume 22, Issue 2, Pages 79–83, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: 10.1515/hc-2015-0279, March 2016

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This article offers supplementary material which is provided at the end of the article.


A facile access to 3-alkyl-5-N-allylamino-2-N′-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement is reported. Alkylation of 5-allylamino-4-benzoyl-1,2,4-triazole-3-thione with alkyl halides in basic alcohol solution is regioselective. A mechanism for the formation of a 1,3,4-thiadiazole ring by 1,2,4-triazole recyclization is proposed. The obtained compounds were characterized by NMR, elemental analysis and X-ray diffraction analysis.

Keywords: alkylation; Dimroth rearrangement; 1,3,4-thiadiazole; 1,2,4-triazole

Supplementary Article Materials

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