Preparing glycosyl benzothiazoles from 2-isocyanoaryl thioethers and glycosyl radicals under thermal conditions
Daqi Liu1, Yang Zhang1, Dawen Niu1
1Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering, Sichuan University, Chengdu 610041, China. zhyang@scu.edu.cn.
Abstract:
Herein, we report a method for preparing glycosyl benzothiazoles via radical cascade cyclization, in which glycosyl radicals are generated from readily available and bench-stable allyl glycosyl sulfones. This cascade reaction proceeds under simple conditions and tolerates a broad substrate scope in high yield with excellent stereoselectivity. Mechanistic studies support that the reactions proceed via the intermediacy of imidoyl radicals, which attack the appended sulfide unit by a SH2 process to forge the thiazole ring.
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