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Current Organic Synthesis
ISSN (Print): 1570-1794
ISSN (Online): 1875-6271
VOLUME: 11
ISSUE: 1
DOI: 10.2174/1570179411999140304143341









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

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Author(s): Xiao-Guang Gao, Ni-Tao Zhanga, Cheng-Chu Zeng, Yong-Dong Liu, Li-Ming Hu and Hong-Yu Tian
Pages 141-148 (8)
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.
Affiliation:
College of Life Science & Bioengineering, Beijing University of Technology, Beijing 100124, China.