Synthesis of Thiazole-2(3<i>H</i>)-ones via [3,3]-Sigmatropic Rearrangement/5-<i>exo</i>-dig Cyclization of <i>N</i>-Propargylamines
Bipin Kumar Behera, Sudip Shit, Subhamoy Biswas, Anil K. Saikia
Abstract
An efficient methodology has been developed for the synthesis of both di- and trisubstituted thiazol-2(3H)-ones from N-propargylamines and silver(I) trifluoromethanethiolate (AgSCF3) in good yields. The reaction proceeds via [3,3]-sigmatropic rearrangement/5-exo-dig 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.
Topics & Concepts
DigSigmatropic reactionThiazoleChemistryCombinatorial chemistryMedicinal chemistryStereochemistryComputer scienceComputer securitySulfur-Based Synthesis TechniquesCyclopropane Reaction MechanismsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry