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, Hong-Yu Tian.

Journal Name:Current Organic Synthesis

Volume 11 , Issue 1 , 2014

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: 1
Year: 2014
Page: [141 - 148]
Pages: 8
DOI: 10.2174/1570179411999140304143341