Green Electrochemical Synthesis of N-Phenylquinoneimine Derivatives: Dual Action of 4-Morpholinoaniline and N-(4-Aminophenyl) Acetamide,ACS Sustainable Chemistry & Engineering

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Green Electrochemical Synthesis of N-Phenylquinoneimine Derivatives: Dual Action of 4-Morpholinoaniline and N-(4-Aminophenyl) Acetamide
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2017-09-20 00:00:00 , DOI: 10.1021/acssuschemeng.7b02553
Mahdi Jamshidi ₁ , Davood Nematollahi ₁

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In this paper, two green electrochemical strategies for the synthesis of new N-phenylquinoneimine derivatives are reported. In the first strategy, the electrophilic activity of electrochemically generated quinone–diimine derivatives was used in reaction with phenol as a model nucleophile. In the second strategy, the electrochemically formed 4-tert-butyl-o-benzoquinone was used as a model Michael acceptor in the reaction with 4-morpholinoaniline, N-(4-aminophenyl) acetamide, and fast violet B. The reaction mechanism in both strategies is electron transfer−chemical reaction−electron transfer/disproportionation (ECE/DISP). This study provided some new N-phenylquinoneimine derivatives in good yields by a one-pot reaction under ambient conditions without toxic reagents.

中文翻译：

N-苯基醌亚胺衍生物的绿色电化学合成：4-Morpholino苯胺和N-（4-氨基苯基）乙酰胺的双重作用

本文报道了两种合成新的N-苯基醌亚胺衍生物的绿色电化学策略。在第一种策略中，电化学生成的醌-二亚胺衍生物的亲电活性用于与作为模型亲核试剂的苯酚反应。在第二种策略中，将电化学形成的4-叔丁基-邻-苯醌用作模型Michael受体，用于与4-吗啉代苯胺，N-（4-氨基苯基）乙酰胺和快速紫B的反应。两种策略都是电子转移-化学反应-电子转移/歧化（ECE / DISP）。这项研究提供了一些新的ñ-苯醌亚胺衍生物，在环境条件下，通过一锅法反应，无毒，收率高。

更新日期：2017-09-20

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