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Communication | Regular issue | Vol 36, No. 7, 1993, pp.1483-1488
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6368
A Regiospecific Synthesis of Carbazoles via Consecutive Palladium-catalyzed Cross-Coupling and Aryne-mediated Cyclization

Masatomo Iwao,* Hirokazu Takehara, Sunao Furukawa, and Mitsuaki Watanabe*

*Faculty of Liberal Arts, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions. The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.