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Communication | Regular issue | Vol 24, No. 7, 1986, pp.1845-1847
Published online, 1st January, 1970
DOI: 10.3987/R-1986-07-1845
Condensed Heteroaromatic Ring System. X. Synthesis of Benzindoles from o-Bromonaphthylamines

Takao Sakamoto, Yoshinori Kondo, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Benz[f]indole, of which few effective preparative methods are known, was easily synthesized by palladium-catalyzed reaction of ethyl 3-bromo-2-naphthylcarbamate with trimethylsilylacetylene and subsequent cyclization with sodium ethoxide in ethanol. By the same method, benz[g]indole and benz[e]indole were obtained from 2-bromo-1-naphthylcarbamate and 1-bromo-2-naphthylcarbamate, respectively.