Masked mercapto acid-driven MCR in task-specific ionic liquid: a new sterocontrolled entry into bicyclic 1,3-thiazines

An unprecedented multi-component reaction for the synthesis of thiosugar-annulated 1,3-thiazines is reported. The envisaged synthetic strategy involves the reaction of d-glucose/d-xylose and 2-methyl-2-phenyl-1,3-oxathiolan-5-one with AcONH4/RNH2 in task specific ionic liquid (TSIL), [bmim]SCN which afforded thiosugar annulated 1,3-thiazines in excellent yields (83-93%). The reaction is effected via ionic liquid promoted Michael addition followed by mercaptoacetylative ring transformation in a one-pot procedure and the ionic liquid, [bmim]OH could be easily recycled for further use without any loss of efficiency and be used for the synthesis of [bmim]SCN, thus allowing recycling of the TSIL for further use.