Rapid and Facile Synthesis of Isomaleimides: Dehydration of Maleamic Acids using Methanesulfonyl Chloride

Abstract

AbstractThe dehydration of maleamic acids using methanesulfonyl chloride as a dehydrating agent to selectively and rapidly (<15 min) generate isomaleimides is reported. A variety of maleamic acid derivatives produce the corresponding isomaleimides in good to excellent yields. Adaptation of this protocol under flow synthesis allows for similar efficiency and decreased reaction times (13 seconds residence time). It was also possible to convert maleic anhydride into the desired isomaleimide in a two-step, one-flask operation.