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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2279-2287
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7177
A New Synthesis of 3-Substituted Indolines and Indoles

Masaru Kihara,* Yasumasa Iwai, and Yoshimitsu Nagao

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770, Japan

Abstract

3-Phenyl- and 3-alkyl-3-hydroxyindolines were synthesized by intramolecular Barbier reaction of phenyl and alkyl N-(2-iodophenyl)-N-methylaminomethyl ketones with n-BuLi, which were easily prepared from N-methyl-2-iodoaniline and bromomethyl ketones. The treatment of the indolines with acid gave the corresponding indoles in quantitative yields.