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Paper | Special issue | Vol 30, No. 1, 1990, pp.451-462
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S21
The Nicholas Reaction of Indoles. Propargylation of Indoles with (Propargyl)dicobalt Hexacarbonyl Cations

Masako Nakagawa,* Jian Ma, and Tohru Hino*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Indole reacted with (propargyl alcohol)Co2(CO)6 complex 1 to give 3-(1,1-dimethylpropargyl)indole 3, whereas N’-methoxycarbonyltryptamine 7 gave the corresponding N-substituted derivative 11. The reaction of 7 with (propargyl acetate)Co2(CO)6 complex 23 provided 3a-(1,1-dimethylpropargyl)hexahydropyrroloimidole cobalt complex 9. Oxidative demetalation of 3, 11, and 9 with Fe(NO3)3 gave 5, 13, and 27, respectively. Hydrogenation of 5 afforded the corresponding 3-(1,1-dimethylallyl)indole 6.