Abstract
AbstractThe combination of chlorotrimethylsilane and NaI is disclosed as a reducing system for protodehalogenation of benzothiazole and thiazole derivatives; surprisingly, the alkoxy groups present in the system are unaffected. The optimized reaction conditions tolerate various functional groups and display good efficiency in the regioselective protodehalogenation of a variety of benzothiazole and thiazole derivatives. In addition, the potential application of the protocol was examined by comparing it with previously developed methods; in most of the cases, the present strategy resulted in better yields under milder condition. The mechanistic studies suggest that the reaction probably proceeds through a radical pathway.
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