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

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

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: tmiurasbchem.kyoto-u.ac.jp, murakamisbchem.kyoto-u.ac.jp

T. Miura, Y. Funakoshi, Y. Fujimoto, J. Nakahashi, M. Murakami, Org. Lett., 2015, 17, 2454-2457.

DOI: 10.1021/acs.orglett.5b00960

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Abstract

1-sulfonyl-1,2,3-triazoles react with thionoesters in the presence of a rhodium(II) catalyst providing 3-sulfonyl-4-thiazolines, which subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.

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Key Words

thiazoles

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ID: J54-Y2015