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Paper | Regular issue | Vol 29, No. 4, 1989, pp.783-794
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4888
Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 2

Hideaki Muratake and Mitsutaka Natsume*

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


General Procedure for synthesizing alkylindoles (14) was developed by cyclization of 12 in i-PrOH using H2SO4 as a catalyst to 1-tosylindoles (13), whose protecting group was reductively cleaved with Mg in MeOH. 7-t-Alkylindoles (23 and 24) were synthesized by removal of the tosyl group of 26 and 35 in advance, followed by treatment of the resulting 34 and 36 with p-TsOH in refluxing C6H6.