l-Proline-catalysed synthesis of 2-aryl-2H,5H-thiopyrano[2,3-b] thiochromen-5-ones from 4-hydroxydithiocoumarins and cinnamaldehyde derivatives

Abstract

The hitherto unreported synthesis of 2-aryl-2H,5H-thiopyrano[2,3-b]thiochromen-5-one derivatives was achieved from 4-hydroxydithiocoumarin and cinnamaldehyde using 20 mol% L-proline, an environmentally benign organocatalyst in methanol under reflux conditions. The current approach involves imine formation, followed by a Mannich reaction, instead of a 1,4-addition or thia-Michael reaction, and finally, cyclization. The salient features of this method are mild reaction conditions, broad substrate scope, good yield, atom economy, and shorter reaction time.