SCHEDULED MAINTENANCE
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.
- This article is part of the themed collection: Celebrating 175 years of IIT Roorkee
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