Thiophenol-catalyzed Claisen rearrangement and radical cyclization: formation of furo- and pyrano-coumarin derivatives

Regioselective synthesis of dihydrofurocoumarins and dihydropyranocoumarins in excellent yields from 4-prop-2-ynyloxy coumarin via a thiol mediated radical reaction is described. Alkenyl radicals are generated from easily available terminal alkynes and thiophenol. Thiophenol catalyzed the Claisen rearrangement of the 4-prop-2-ynyloxycoumarin ethers. (c) 2007 Elsevier Ltd. All rights reserved.