Novel synthesis of benzothiazole derivatives via directed lithiation and aryne-mediated cyclization followed by quenching with electrophiles

Article abstract of DOI:10.1021/jo960203z

A series of benzothiazole derivatives selectively functionalized at position 7 was synthesized in the course of the following one-pot reaction sequence: directed lithiation of 2,2-dimethyl-N-(3-halophenyl)propanethioamides (1, 2) or N-(3-halophenyl)-tert-butylthionocarbamates (15-17), cyclization of the aryne intermediate, and quenching of the resulting aryllithium with selected electrophiles.