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Paper | Regular issue | Vol 32, No. 7, 1991, pp.1377-1386
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5761
A New Synthesis of N-Tosylindole from Aniline via ortho-Substituted N-Tosylanilides

Yasushi Murai, Gen Masuda, Seiichi Inoue,* and Kikumasa Sato

*Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Yokohama National University, Tokiwadai 156, Hodogaya-ku, Yokohama 240-8501, Japan

Abstract

A simple and very efficient synthesis of N-tosylindole is described, based on the acid-catalyzed cyclization of ortho-alkylated N-tosylanilides, which can be prepared from aniline and dialkyl sulfide by [2,3]sigmatropic rearrangements.