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Anodic cyanation of 1-arylpyrroles

✍ Scribed by Wei Liu; Yuan Ma; Yu-Fen Zhao; Ying-Wu Yin

Book ID
102345910
Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
257 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The electrooxidation of several 1‐arylpyrroles has been carried out in methanol containing sodium cyanide at a platinum anode in a divided cell. In all instances, replacement of a heteroaromatic hydrogen by a cyano group occurred. On the basis of electroanalytical results, the anodic cyanation of the title compounds could be designed an EC process. As a result of two‐electron oxidation, the corresponding pyrrole cyanides were obtained in yields ranging from 76‐85%. The advantages of electrochemistry synthesis of pyrrole cyanides are simple reaction condition, low cost and high purity products.

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## Abstract α‐Cyano‐__N__‐alkyl‐1‐benzazepines are obtained by electrochemical oxidation of various 1‐benzazepines. Electrolyses are carried out in a flow cell, at a carbon felt anode in methanol; the supporting electrolyte is a mixture of lithium acetate and sodium cyanide. With 2,3,4,5‐tetrahydro