An efficient tandem aldol condensation-thia-Michael addition process

An efficient synthesis of beta-aryl-beta-mercapto ketones is achieved via a tandem aldol condensation-thia-Michael addition process using an aqueous medium and diethylamine. Addition of different thiols to alpha,beta-unsaturated ketones, formed in situ from the condensation of acetophenone derivatives with aldehydes, led to a rapid and high yielding synthesis of the products under very mild conditions using no expensive additive or catalyst. Products which precipitated spontaneously in the reaction mixtures were separated by simple filtration and purified by recrystallization. (c) 2012 Elsevier Ltd. All rights reserved.