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

• Published in: Organic & biomolecular chemistry Vol. 21; no. 12; pp. 2524 - 253
• Main Authors: Aich, Shobhon, Nandi, Rajesh, Chatterjee, Nirbhik, Gayen, Krishnanka S, Pal, Subhasis, Maiti, Dilip K
• Format: Journal Article
• Published: 22.03.2023
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00165b

We developed an efficient and straightforward I 2 -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(sp 3 )-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. 1 H 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. We report a method of coupling of benzimidates and acetophenones mediated by catalytic I 2 and moist DMSO to furnish α-amidohydroxyketones as well as symmetrical and unsymmetrical bisamides. Promising recognition properties of α-amidohydroxyketones were established.