Base-controlled regioselective synthesis of 2imino thiazolines and 2-thioxoimidazolin-4-ones was achieved to use a one-pot reaction between chiral amino esters, isothiocyanates, and α-bromoketones/alkyl halides. This three-component coupling reaction in acetonitrile provides 2-imino thiazolines, whereas the formation of 2-thioxoimidazolin-4-ones was observed under basic conditions at ambient temperature. The corresponding products were obtained in good to excellent yield with broad substrate scope. Isolation of thiourea and thiohydantoin intermediates disclosed the course of the reaction mechanism.
Regioselective One-Pot Three Component Synthesis of Chiral 2-Iminoselenazolines under Sonication. -A regioselective, ultrasound-promoted synthesis of substituted 2-iminoselenazoles is presented. In situ generated selenoureas react in a Hantzsch selenazole-type reaction with -bromo-ketones at room temperature. -(CHANG, W.-J.; KULKARNI, M. V.; SUN*, C.-M.; RSC Adv. 5 (2015) 118, 97113-97120, http://dx.
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