Microwave-assisted fluorous synthesis of 2-aryl-substituted 4-thiazolidinone and 4-thiazinanone libraries.

A straightforward two-step protocol for the synthesis of 2-aryl-substituted 4-thiazolidinone and 4-thiazinanone libraries has been developed. The one-pot, three-component reactions of fluorous benzaldehydes with amines and mercaptoacetic acid or mecaptopropanoic acid produce the heterocyclic systems. Intermediates purified by fluorous solid-phase extraction are subject to microwave-assisted palladium-catalyzed coupling reactions to simultaneously cleave the fluorous tag and introduce the biaryl and thioaryl functional groups to the 2-position of 4-thiazolidinones and 4-thiazinanones.