Preparation of 2-sulfonyl-1,2,3-triazoles by base-promoted 1,2-rearrangement of a sulfonyl group

Motoshi Yamauchi, Tomoya Miura, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

1,2-Rearrangement of a sulfonyl group occurs on treatment of 1-sulfonyl-1,2,3-triazoles with a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile to give an equilibrium mixture of 1-sulfonyl- and 2-sulfonyl derivatives, with considerable predominance of the latter. Subsequent acidic treatment of the mixture caused selective hydrolysis of the 1-sulfonyl derivative, which led to the isolation of the 2-sulfonyl-1,2,3-triazole in good total yield in a pure form.

Original languageEnglish
Pages (from-to)177-181
Number of pages5
JournalHeterocycles
Volume80
Issue number1
DOIs
Publication statusPublished - Jan 1 2010
Externally publishedYes

Keywords

  • 1,2,3-Triazole
  • Base-Promoted Reaction
  • Rearrangement
  • Regioselective Reaction
  • Sulfonyl Group

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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