New strategy for indole synthesis from ethyl pyrrole-2-carboxylate (synthetic studies on indoles and related compounds. XXXIX)

DOI: 10.1248/cpb.44.55

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Chemical and Pharmaceutical Bulletin p. 55 - 61 (1996)

Update date:2022-09-26

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Authors:

Tani, Masanobu

Ariyasu, Takahiro

Ohtsuka, Masanori

Koga, Terumi

Ogawa, Yumi

Yokoyama, Yuusaku

Murakami, Yasuoki

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Article abstract of DOI:10.1248/cpb.44.55

As a synthetic application of the previously reported C₄-acylation of ethyl pyrrole-2-carboxylate (1), a new strategy for indole synthesis was developed. Ethyl pyrrole-2-carboxylate (1) was allowed to react with succinic anhydride or 3-methoxycarbonylpropionyl chloride to give, in good yield, a C₄-succinyl derivative of 1, which was converted into ethyl 7-oxo-4,5,6,7- tetrahydroindole-2-carboxylate (6) as a key intermediate for indole synthesis. Starting from 6, several indoles functionalized on the benzene moiety were synthesized.

Full text of DOI:10.1248/cpb.44.55

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