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Paper | Regular issue | Vol 92, No. 11, 2016, pp.2004-2017
Published online, 14th October, 2016
DOI: 10.3987/COM-16-13544
Synthesis of New 3-Substituted 1-Hydroxy-2-phenylindoles Using Sulfur-Containing Nucleophiles

Hyejin Kim and Sang Hyup Lee*

*College of Pharmacy and Innovative Drug Center, Duksung Women's University, Seoul 01369, Korea

Abstract

The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2- phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2·2H2O, with nucleophiles such as thiocarboxylic acids and thiols to provide target compounds 1 by successive processes of nitro reduction and intramolecular condensation, followed by addition of nucleophile. Analyses of the reaction mechanism, including the effects of substituents along with the reactivity of nucleophiles, are described.