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

Authors

  • Лидия Н. Дианова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Татьяна В. Березкина Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Валерий О. Филимонов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia
  • Джи Джин Фан State Key Laboratory of Elemento organic Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, China
  • Павел А. Слепухин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108, Russia
  • Василий А. Бакулев Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia

DOI:

https://doi.org/10.1007/5821

Keywords:

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

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.

Author Biography

Василий А. Бакулев, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia

The chief of the technologyfor Organic Synthesis Department

Published

2020-11-05

Issue

Section

Original Papers