Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters

Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

68 Citations (Scopus)

Abstract

A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)2454-2457
Number of pages4
JournalOrganic Letters
Volume17
Issue number10
DOIs
Publication statusPublished - May 15 2015
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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