Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and Lawesson's reagent.

Qiuping Ding, Xi-Gen Huang, Jie Wu

Index: J. Comb. Chem. 11(6) , 1047-9, (2009)

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Abstract

In the presence of Lawesson's reagent, metal-free one-pot cascade reactions of 2-iodoanilines with acid chlorides proceeded smoothly leading to 2-substituted benzothiazoles in good to excellent yields under mild conditions. Three steps were involved in the reaction process: (1) 2-iodoanilines reacted with acid chlorides to afford benzamides, (2) benzamides transferred to benzothioamides in the presence of Lawesson's reagent, and (3) intramolecular cyclization of benzothioamides generated the expected benzothiazoles.