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

作者:Miura Tomoya*; Funakoshi Yuuta; Fujimoto Yoshikazu; Nakahashi Junki; Murakami Masahiro
来源:Organic Letters, 2015, 17(10): 2454-2457.
DOI:10.1021/acs.orglett.5b00960

摘要

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.

  • 出版日期2015-5-15