Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals

ISSN: 1875-6271 (Online)
ISSN: 1570-1794 (Print)


Volume 11, 6 Issues, 2014


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Current Organic Synthesis

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Prof. Eduardo A Castro
Universidad Nacional de La Plata
Buenos Aires
Argentina


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Electrochemical Synthesis of Polyfunctionalized Indoles in Aqueous Medium from Catechols and Ketene N,S-acetals

Author(s): Xiao-Guang Gao, Ni-Tao Zhanga, Cheng-Chu Zeng, Yong-Dong Liu, Li-Ming Hu and Hong-Yu Tian

Affiliation: College of Life Science & Bioengineering, Beijing University of Technology, Beijing 100124, China.

Abstract

The electrochemical synthesis of o-benzoquinones and their in situ transformation is a versatile approach for the synthesis of polyhydroxylated aromatics. In the present paper, the electrochemical oxidation of catechol in the presence of ketene N,S-acetals as N,Cdoubly nucleophiles was first investigated using cyclic voltammetry technique. Then preparative scale of electrolysis was carried out to demonstrate that polyfunctionalized indoles could be one-pot synthesized under constant current electrolysis conditions. Finally, the reaction mechanism was proposed.

Keywords: Anodic oxidation, catechols, ketene N, S-acetals, polyhydroxylated indoles.

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Article Details

Volume: 11
Issue Number: 1
First Page: 141
Last Page: 148
Page Count: 8
DOI: 10.2174/1570179411999140304143341
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