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Paper | Regular issue | Vol 60, No. 9, 2003, pp.2095-2101
Published online, 4th August, 2003
DOI: 10.3987/COM-03-9832
Synthesis of Naphth[3,2,1-cd]indole by Heck Cyclization of 2-Methoxycarbonyl-3-benzoylindoles

Yasuyoshi Miki,* Hideaki Shirokoshi, Mikito Asai, Yoshiyuki Aoki, and Hana Matsukida

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with 1,3-dimethoxybenzene in the presence of titanium(IV) chloride gave the corresponding 3-(2,4-dimethoxybenzoyl)indole-2-carboxylic acid as the sole product. This carboxylic acid could be converted to naphth[3,2,1-cd]indole.