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Paper | Special issue | Vol 61, No. 1, 2003, pp.163-172
Published online, 21st May, 2003
DOI: 10.3987/COM-03-S11
Nucleophilic Substitution Reaction at the 1-Position of 1-Hydroxytryptamine and -tryptophan Derivatives

Fumio Yamada, Aya Goto, Wu Peng, Toshikatsu Hayashi, Yoshitomo Saga, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


A novel nucleophilic substitution reaction at the 1-position of indole nucleus was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed.