Synthetic Studies on Indoles and Related Compounds. XXV. The Friedel-Crafts Acylation of Ethyl 1H-Indole-2-carboxylate. (2)

Masanobu TANI; Tsuyoshi AOKI; Sadao ITO; Shigenobu MATSUMOTO; Mami HIDESHIMA; Kaoru FUKUSHIMA; Ryoichi NOZAWA; Takako MAEDA; Mayumi TASHIRO; Yuusaku YOKOYAMA; Yasuoki MURAKAMI

doi:10.1248/cpb.38.3261

Masanobu TANI, Tsuyoshi AOKI, Sadao ITO, Shigenobu MATSUMOTO, Mami HIDESHIMA, Kaoru FUKUSHIMA, Ryoichi NOZAWA, Takako MAEDA, Mayumi TASHIRO, Yuusaku YOKOYAMA, Yasuoki MURAKAMI

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Keywords: Friedel-Crafts reaction, ethyl 1H-indole-2-carboxylate, acylation, regioselectivity, aluminum chloride, N-benxylindole

JOURNAL FREE ACCESS

1990 Volume 38 Issue 12 Pages 3261-3267

DOI https://doi.org/10.1248/cpb.38.3261

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Abstract

The Friedel-Crafts acylation of ethyl 1H-indole-2-carboxylate (1) with various acylating reagents having a functional group or hetero atom and the acylation of some derivatives (6, 7, 8, and 9) of ethyl 1H-indole-2-carboxylate (1) with simple acylating reagents are described. Acylation occurred at the C₃-position or on the benzene moiety (mainly at the C₅-position) of the indole nucleus. The regioselectivity of the above acylation of indoles (1, 6, 7, 8, and 9) is discussed.

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