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Heterocyclic Communications

Editor-in-Chief: Strekowski, Lucjan

Ed. by Murata, Shizuaki / Saczewski, Jaroslaw / Stephens, Chad

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Volume 21, Issue 6 (Dec 2015)

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Synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts via regioselective electrophilic cyclization of 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles

1 / Nataliya Korol1 / Ivan Rusyn1 / Vasyl Lendel1

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

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

Citation Information: Heterocyclic Communications. Volume 21, Issue 6, Pages 397–401, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: 10.1515/hc-2015-0158, November 2015

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Publication History

Received:
2015-08-10
Accepted:
2015-10-27
Published Online:
2015-11-26

Abstract

A convenient procedure for the regioselective preparation of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium 10 and [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium salts 9 via regioselective electrophilic cyclization of 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles 3 is reported. Direction of electrophilic heterocyclization strongly depends on nature of the alkenyl substitutent.

Keywords: electrophilic cyclization; halogen; regioselectivity; selenium tetrahalogenides; tellurium tetrahalogenides; [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium; [1,2,4]triazolo[5,1-b][1,3]thiazin-4-ium

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