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

ABSTRACT: An efficient methodology has been developed for the synthesis of both di- and trisubstituted thiazol-2(3H)-ones from Npropargylamines and silver(I) trifluoromethanethiolate (AgSCF3) in good yields. The reaction proceeds via [3,3]-sigmatropic rearrangement/5-exodig cyclization of N-propargylamines. The starting material can be easily prepared from the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can be extended for the synthesis of thiozole-2(3H)thione derivatives, and photophysical properties have been studied for some synthesized compounds.

Automated summary

An efficient methodology for the synthesis of di- and trisubstituted thiazol-2(3H)-ones from N-propargylamines and silver(I) trifluoromethanethiolate has been developed. The reaction proceeds through [3,3]-sigmatropic rearrangement/5-exodig cyclization of N-propargylamines. The starting material can be easily prepared via the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can also be extended to the synthesis of thiozole-2(3H)thione derivatives, and the photophysical properties of some synthesized compounds have been studied.