A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3 H)-one

J Org Chem. 2024 Nov 7. doi: 10.1021/acs.joc.4c01800. Online ahead of print.

Abstract

A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3H)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.