Chemical and Pharmaceutical Bulletin p. 55 - 61 (1996)
Update date:2022-09-26
Topics:
Tani, Masanobu
Ariyasu, Takahiro
Ohtsuka, Masanori
Koga, Terumi
Ogawa, Yumi
Yokoyama, Yuusaku
Murakami, Yasuoki
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.
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