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Communication | Regular issue | Vol 55, No. 3, 2001, pp.457-460
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9135
Nucleophilic Substitution Reaction on the Nitrogen of Indole Nucleus: Formation of 1-(Indol-3-yl)indoles upon Reaction of 1-Hydroxyindoles with Indole in Formic Acid

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

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

Abstract

1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanism on the indole nitrogen is proposed.