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Paper | Regular issue | Vol 29, No. 4, 1989, pp.771-782
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4887
Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 1

Hideaki Muratake and Mitsutaka Natsume*

*Research Foundation Itsuu Laboratory, 2-28-10 Tamagawa, Setagaya-ku, Tokyo 158, Japan

Abstract

Variously alkylated 4-(1-methoxycarbonyl-2-pyrroly1)-2-butenals (11 and 12) were cyclized to 1-methoxycarbonylindoles (14) having alkyl substituents in the benzene portion, simply by refluxing in benzene solution with a catalytic amount of p-TsOH. A natural product, 7-(3-methyl-2-butenyl)indole (27) was synthesized by this technique, whereas the corresponding 6-isomer (28), also a natural product, was obtained by treatment of 32 with TMSOTf.