Electrochemical oxidation of 4-(piperazin-1-yl)phenols in the presence of indole derivatives: The unique regioselectivity in the synthesis of highly conjugated bisindolyl-p-quinone derivatives

被引：18
作者：
Amani, Amene [1 ]
Khazalpour, Sadegh [1 ]
Nematollahi, Davood [1 ]
机构：
[1] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran
来源：
JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 2012年 / 670卷
关键词：
Electrochemical synthesis; 4-(Piperazin-1-yl)phenols; Bisindolyl-p-quinones; Michael type reaction; Cyclic voltammetry; KINETIC EVALUATION; O-BENZOQUINONE; 2,5-DIHYDROXY-3-(INDOL-3-YL)BENZOQUINONES; ACIDS;
D O I：
10.1016/j.jelechem.2012.02.003
中图分类号：
O65 [分析化学];
学科分类号：
070302 ; 081704 ;
摘要：
The electrochemical oxidation of 4-(piperazin-1-yl)phenols have been studied in the presence of indole derivatives as nucleophiles in water/acetonitrile mixture by means of cyclic voltammetry and controlled-potential coulometry. The reaction mechanism is believed to be oxidation of 4-(piperazin-1-yl)phenols, Michael addition reaction, oxidation of the formed adduct, another Michael addition reaction, oxidation of new adduct and hydrolysis (ECECEC). The results revealed that bisindolyl-p-quinones were synthesized through the regioselective addition of indoles to electrochemically generated quinone imines in good yields at carbon electrode in a divided cell. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码：36 / 41
页数：6
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