Facile synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters.
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.
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Tomoya
T
Miura
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Yuuta
Y
Funakoshi
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Yoshikazu
Y
Fujimoto
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Junki
J
Nakahashi
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Masahiro
M
Murakami
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D004952:Esters; D013438:Sulfhydryl Compounds; D013844:Thiazoles