DPPA-mediated One-Pot Cascade Transformation Enables Direct Synthesis of Fluorogenic 2-Aminomaleimides and Thioaminomaleimides

Abstract

A one-pot cascade metal-free and solvent-free strategy for the synthesis of 2-aminomaleimide, thioaminomaleimide, and 2-amidomaleimide directly from maleic anhydride is reported. DFT calculation supports the proposed cascade pathway for the reaction. The method provides an additional site for drug-maleimide conjugation. The fluorogenic and thiol-sensing potential of the synthesized maleimides is also demonstrated.