Open Access Open Access  Restricted Access Subscription Access

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

Лидия Н. Дианова, Татьяна В. Березкина, Валерий О. Филимонов, Джи Джин Фан, Павел А. Слепухин, Василий А. Бакулев
Cover Image

Abstract


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.

Keywords


sulfonyl chlorides; 1,2,3-triazoles; acylation; Dimroth rearrangement; sulfonylation.

Full Text: PDF (Russian) Supplementary File(s): supplementary info (1MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv