Aqueous versus Neat Reaction Conditions: The Microwave-Assisted, Selective Conversion of a Fused Anhydride Ring with Amines in the Presence of a Keto Group

Abstract

We describe the transformation of fused succinic anhydride derivatives of the bicyclo[2.2.2]oct-2-ene system with various amines under microwave-irradiation conditions. In aqueous suspensions, the reaction of an acetyl-containing derivative yielded chemoselectively succinimide derivatives with the acetyl group remaining unchanged. Conversely, the application of neat reaction conditions with a minor amount of a liquid additive (toluene) yielded succinimide derivatives with the acetyl moiety transformed into an imine group.