Solvent-controlled regioselective iodocyclization of propargylic amides

Abstract

The development of controllable reactions, due to their particularity of generating diverse products from a single starting material, has long been an important research area in organic synthesis. In this study, a solvent-controlled electrophilic iodocyclization reaction of propargylic amides has been developed, enabling the highly regioselective synthesis of oxazolidine-2,4-dione and 1,3-oxazine-2,4-dione compounds. Both types of products could be synthesized with high yields and good functional group tolerance. In terms of the mechanism, we hypothesize that the polarity of the solvent plays a crucial role in the regioselective control.