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Thiazole Synthesis by Cyclocondensation of 1‐Alkynyl(phenyl)‐ λ 3 ‐iodanes with Thioureas and Thioamides
Author(s) -
Miyamoto Kazunori,
Nishi Yoshio,
Ochiai Masahito
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502438
Subject(s) - hypervalent molecule , thiazole , chemistry , nucleophile , intramolecular force , sulfur , medicinal chemistry , michael reaction , organic chemistry , catalysis , iodine
The isolation and intramolecular cyclization of ( S )‐(1‐alkynyl)isothiouronium and ( S )‐(1‐alkynyl)thiobenzimidonium salts suggest the mechanism for the one‐pot synthesis of 2,4‐disubstituted thiazoles (see scheme; Ms=methanesulfonyl): Michael addition of sulfur nucleophiles to hypervalent iodanes followed by the 1,2‐rearrangement of sulfenyl groups in the resulting alkylidene carbenes.