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Paper | Regular issue | Vol 60, No. 7, 2003, pp.1589-1600
Published online, 28th April, 2003
DOI: 10.3987/COM-03-9766
Nucleophilic Substitution Reaction of N-2-(1-Hydroxyindol-3-yl)ethylindole-3-acetamide and -1-hydroxyindole-3-acetamide

Yu-ya Nakai, Aya Goto, Fumio Yamada, and Masanori Somei*

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


Syntheses of N-2-(1-hydroxyindol-3-yl)ethyl-1-hydroxyindole-3-acetamide (3a) and -indole-3-acetamide (4a) are reported. They undergo nucleophilic substitution reaction at the 1-position upon reaction with indole in 85% formic acid to give new type compounds, N-2-[1-(indol-3-yl)indol-3-yl]ethylindole-3-acetamide (13), N-2-(indol-3-yl)ethyl- (14), and N-2-[1-(indol-3-yl)indol-3-yl]ethyl-1-(indol-3-yl)indole-3-acetamide (15).