TY - JOUR
T1 - Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
AU - Miura, Tomoya
AU - Funakoshi, Yuuta
AU - Fujimoto, Yoshikazu
AU - Nakahashi, Junki
AU - Murakami, Masahiro
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/5/15
Y1 - 2015/5/15
N2 - 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).
AB - 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).
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U2 - 10.1021/acs.orglett.5b00960
DO - 10.1021/acs.orglett.5b00960
M3 - Article
C2 - 25927965
AN - SCOPUS:84929600754
SN - 1523-7060
VL - 17
SP - 2454
EP - 2457
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -