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 tolerance. In terms of the mechanism, we hypothesize that the polarity of the solvent plays a crucial role in the regioselective controlling.