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Synthesis 2010(12): 1983-1988  
DOI: 10.1055/s-0029-1218798
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles

D. Subhas Bose*, Mohd. Idrees
Organic Chemistry Division III, Fine Chemicals Laboratory, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160387; e-Mail: dsb@iict.res.in; e-Mail: bose_iict@yahoo.co.in;
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Publication History

Received 23 February 2010
Publication Date:
27 May 2010 (online)

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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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