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Paper | Special issue | Vol 77, No. 2, 2009, pp.971-982
Published online: 2nd October, 2008
DOI: 10.3987/COM-08-S(F)71
Nucleophilic Substitution Reaction in Indole Chemistry: 1-Methoxy-6-nitroindole-3-carbaldehyde as a Versatile Building Block for 2,3,6-Trisubstituted Indoles

Koji Yamada, Fumio Yamada, Takei Shiraishi, Saori Tomioka, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position with various types of nucleophiles providing 2,3,6-trisubstituted indole derivatives. The reaction is applicable for the preparation of a novel pyrimido[1,2-a]indole derivative.

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