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Communication | Special issue | Vol 58, No. 1, 2002, pp.75-78
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S(M)27
Regioselective Synthesis of 2,3,5-Trisubstituted Indoles from p-Sulfinylaniline by Dual Use of the Sulfinyl Group

Shuji Akai, Norihito Kawashita, Nobuyoshi Morita, Yuka Nakamura, Kiyosei Iio, and Yasuyuki Kita*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


A novel and convergent synthesis of 2,3,5-trisubstituted indoles (6) from p-sulfinylaniline (1) is described. The single p-sulfinyl group was repeatedly employed in two ways; viz., the construction of the 2,3-disubstituted indole/indoline skeleton and the introduction of a carbon substituent at the C-5 position.