Catalytic I2-moist DMSO-mediated synthesis of valuable α-amidohydroxyketones and unsymmetrical gem-bisamides from benzimidates

Abstract

We developed an efficient and straightforward I₂-catalyzed strategy for the synthesis of functionalized α-amidohydroxyketones and symmetrical and unsymmetrical bisamides using incipient benzimidate scaffolds as starting materials and moist-DMSO as a reagent and solvent. The developed method proceeds through chemoselective intermolecular N–C-bond formation of benzimidates and the α-C(sp³)–H bond of acetophenone moieties. The key advantages of these design approaches include broad substrate scope and moderate yields. High-resolution mass spectrometry of the reaction progress and labeling experiments provided suitable evidence regarding the possible mechanism. ¹H nuclear magnetic resonance titration revealed notable interaction between the synthesized α-amidohydroxyketones and some anions as well as biologically important molecules, which revealed a promising recognition property of these valuable motifs.