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DOI: 10.1055/s-0029-1218798
Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles
Publication History
Publication Date:
27 May 2010 (online)

Abstract
Carbon-fluorine bond fission has been coupled with C-S bond formation under metal-free conditions, which is seldom reported in the literature. The intramolecular C-S bond formation reaction takes place by fission of the carbon-fluorine bond in situ, and is believed to proceed through an SNAr mechanism. The approach represents a practical and atom-economical approach for regioselective and metal-free cascade synthesis of substituted benzothiazoles. This one-pot, environmentally benign protocol involves 2-fluoroanilines, benzoyl chlorides and Lawesson’s reagent under microwave irradiation (5 min) or conventional thermal conditions (3 h).
Key words
benzothiazole - metal-free - cascade reactions - S-arylation - regioselective
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