Regio- and stereoselective synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts via electrophilic heterocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles and their antimicrobial activity

Heterocyclic communications

article

Mikhailo Slivka¹  Nataliya Korol¹  Valerij Pantyo¹  Vjacheslav Baumer²  Vasil Lendel¹ 

[1] Organic Synthesis Laboratory, Uzhhorod National University;SSI “Institute for Single Crystals” NASU

关键词: electrophilic cyclization;    halogen;    regioselectivity;    stereoselectivity;    tellurium tetrahalogenides;    [1;    3]thiazolo[3;    2-b][1;    2;    4]triazol-7-ium salts;   

DOI  :  10.1515/hc-2016-0233

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

A procedure for the preparation of the title salts via regioselective halocyclization of 3- S -propargylthio-4 Н -1,2,4-triazoles is reported. Stereoselectivity of electrophilic heterocyclization depends on the nature of the electrophilic reagent: bromination is better than iodobromination and iodination. The heterocyclization with tellurium tetrahalogenides leads to the formation of a mixture of geometric isomers of the salts. Their structure was confirmed by 1 H NMR, 13 C NMR, НМВС and single crystal X-ray diffraction analysis.

【 授权许可】

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