The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides

The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-10, Vol.56 (10), p.1341-1347
Main Authors: Dianova, Lidiya N., Beryozkina, Tetyana V., Filimonov, Valeriy O., Fan, Zhijin, Slepukhin, Pavel А., Bakulev, Vasiliy А.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02820-3