One-pot cis-selective route to sugar-fused thiazines via a masking–unmasking strategy in basic ionic liquid

Abstract

A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, d-xylose/d-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim]OH. The acetophenone obtained as a by-product and [bmim]OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.