FeCl3-catalyzed regioselective ring-opening of aryl oxirane with 4-hydroxycoumarin for the synthesis of furo[3,2-c]coumarins.

Abstract

The regioselective ring-opening of aryl oxiranes was investigated with various 4-hydroxycoumarins in dimethyl sulfoxide in the presence of 20 mol% FeCl3 as a catalyst at 110 °C. This approach provided a short and concise synthetic route for the regioselective synthesis of 2-aryl-4H-furo[3,2-c] coumarin derivatives. Product formation occurred through regioselective ring-opening of the aryl oxirane at a less hindered site, followed by dehydration and concomitant cyclization. The salient features of our protocol were: cost-effectiveness; short reaction time; step- and atom economy; easy handling; broad scope of substrates; regioselectivity; good-to-excellent yields; non-requirement of dry solvents, co-catalysts, ligands, or any other additives; inert atmospheric conditions.