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Paper | Special issue | Vol 88, No. 1, 2014, pp.493-520
Published online, 29th July, 2013
DOI: 10.3987/COM-13-S(S)74
Synthesis of 4-Amino-, 4-Hydroxy-, and 4-Nitro-1,3,4,5-tetrahydrobenz[cd]indols and Its Bromination

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

*Noto Marine Laboratory, Institute of Nature and Environmental Technology, Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, 56-7 Matsuhidai, Matsudo-shi, Chiba 270-2214, Japan

Abstract

Simple synthetic method for 4-nitro-1,3,4,5-tetrahydrobenz[cd]indole (6) is established from indole-3-carboxaldehyde (7). With 6 in hand, various derivatives of 4-amino-, 4-hydroxy- and 4-amino-4-hydroxymethyl-1,3,4,5-tetrahydrobenz[cd]indoles become readily available. Bromination of 6 afforded useful building blocks for further manipulation. Successful optical resolution of 6 by chiral column chromatography is also reported.