Synthesis of Thiazole-2(3)-ones via [3,3]-Sigmatropic Rearrangement/5--dig Cyclization of -Propargylamines.

An efficient methodology has been developed for the synthesis of both di- and trisubstituted thiazol-2(3)-ones from -propargylamines and silver(I) trifluoromethanethiolate (AgSCF) in good yields. The reaction proceeds via [3,3]-sigmatropic rearrangement/5--dig cyclization of -propargylamines. The starting material can be easily prepared from the A-coupling reaction of amines, aldehydes, and alkynes. The methodology can be extended for the synthesis of thiozole-2(3)-thione derivatives, and photophysical properties have been studied for some synthesized compounds.