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Communication | Regular issue | Vol 34, No. 12, 1992, pp.2269-2275
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6173
A Simple Four Step Synthesis and Optical Resolution of 4-Nitro-1,3,4,5-tetrahydrobenz[cd]indole, and the Syntheses of 1-Hydroxy Derivatives of 4-Nitro- and 4-Amino-1,3,4,5-tetrahydrobenz[cd]indoles

Kyoko Nakagawa, Naokatsu Aoki, Harunobu Mukaiyama, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920, Japan

Abstract

4-Nitro-1,3,4,5-tetrahydrobenz[cd]indole was synthesized from indole-3-carboxaldehyde in four steps with an overall yield of 30%. Optical resolution of its enantiomers by chiral column chromatography was successful. Syntheses of 1-hydroxy derivatives of 4-nitro- and 4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are also reported.