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Paper | Special issue | Vol 95, No. 2, 2017, pp.920-933
Published online, 29th November, 2016
DOI: 10.3987/COM-16-S(S)60
Simultaneous Functionalization and Cyclization of 2-Ethynylaniline Derivatives to Indoles

Kou Hiroya,* Shin Itoh, Kiyofumi Inamoto, Hiroki Shigehisa, and Takao Sakamoto

*Faculty of Pharmacy, Musashino University, 1-1-20 Shin-machi, Nishitokyo-shi, Tokyo, Japan

Abstract

Two different kind of sequential cyclization-functionalization are developed. Namely, cyclization-chlorination of 2-ethynylaniline derivatives using CuCl2 gave 3-chloro- and 3,5-dichloroindole derivatives. The plausible mechanism for this reaction is also discussed. On the other hand, the reaction between 2-ethynylaniline derivatives and Cu(NO3)2·3H2O in THF provided C4-nitro compound. After being changed the solvent from THF to DMF, followed by heating, 5-nitroindole derivatives was afforded.