Copper-assisted synthesis of dihydropyrano[2.3-b]indole-4-ones by domino cascade reaction

Abstract

A novel copper-catalyzed cascade intermolecular and intramolecular oxidation/cyclization domino one-pot reaction process for the regioselective synthesis of dihydropyrano[2.3-b]indol-4(9H)-ones has been successfully developed. In this methodology, it is proposed for the first time that the 4-benzyloxy group of indole substrates can be used as a guiding group to promote cyclization under mild conditions. Meanwhile, reaction mechanism studies indicate that carbonyl oxygen in pyranoindole-4-ones came from water and the guiding group is critical to the progress of the reaction.