Mechanism of electrochemical oxidation of catechol and 3-substituted catechols in the presence of barbituric acid derivatives. Synthesis of new dispiropyrimidine derivatives

被引：29

作者：

Nematollahi, D ^{[1
]}

Goodarzi, H ^{[1
]}

Tammari, E ^{[1
]}

机构：

[1] Univ Bu Ali Sina, Fac Sci, Dept Chem, Hamadan, Iran

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2002年 / 04期

关键词：

D O I：

10.1039/b106794j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrochemical oxidation mechanism of catechol (1a), 3-methylcatechol (1b) and 3-methoxycatechol (1c) in the presence of barbituric acid (3a) and 1,3-dimethylbarbituric acid (3b) as nucleophile in aqueous solution has been studied in detail by cyclic voltammetry and controlled-potential coulometry. The results indicate that 1a-1c via an ECEC (E, electrochemical; C, chemical) pathway, participating in a 1,4 (Michael) addition reaction, are converted to dispiropyrimidine derivatives 6a-6f. The homogeneous rate constants were estimated by comparing the experimental cyclic voltammetric responses with the digital simulated results. The electrochemical synthesis of 6a-6f has been successfully performed in an undivided cell in good yields and high purity.

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页码：829 / 834

页数：6

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