Photoredox-Promoted Selective Synthesis of C-5 Thiolated 2-Aminothiazoles from Terminal Alkynes
Majid Ahmad Ganie, Muneer‐ul‐Shafi Bhat, Masood Ahmad Rizvi, Shabnam Raheem, Bhahwal Ali Shah
Abstract
A mild photoredox approach enabling the first one-step synthesis of thiolated 2-aminothiazoles has been reported. Notably, the incorporation of thio group on electron-rich heteroarenes such as aminothiazoles via conventional nucleophilic aromatic substitution (SNAr) presents a significant challenge owing to polarity mismatch. Herein, we present a remarkable site-selective installation of thio group at the C-5 position of the electron-rich aminothiazole skeleton and successfully used them for the postfunctionalization of drugs and natural products.
Topics & Concepts
ChemistryNucleophilic aromatic substitutionCombinatorial chemistryThio-Polarity (international relations)NucleophileNucleophilic substitutionStereochemistryMedicinal chemistryOrganic chemistryCatalysisCellBiochemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods