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Paper | Regular issue | Vol 57, No. 9, 2002, pp.1645-1651
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9538
Synthesis of 5H-Benzo[b]carbazole-6,11-diones from Benzoylindolecarboxylic Acids

Yasuyoshi Miki,* Yasuhiko Tsuzaki, and Hana Matsukida

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

Abstract

Treatment of 1-benzyl-3-(4-methoxybenzoyl)indole-2-carboxylic acid with phosphorus pentachloride gave the corresponding acid chloride, which was treated with titanium(IV) chloride to afford 9-methoxy-5H-benzo[b]carbazole-6,11-dione. In a similar manner, 1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid provided 9-methoxy-5H-benzo[b]carbazole-6,11-dione. However, 1-benzyl-3-(4-methoxybenzyl)indole-2-carboxylic acid could be converted to 8-methoxy-5H-benzo[b]carbazole-6,11-dione.