咪唑盐二醋酸碘苯促进苯并咪唑类衍生物的水相合成

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (2): 296.

咪唑盐二醋酸碘苯促进苯并咪唑类衍生物的水相合成

王孝科, 田敉

重庆科技学院化学化工学院, 重庆 401331

收稿日期:2009-04-09 出版日期:2010-02-10 发布日期:2010-02-10
通讯作者: 田敉, 女, 讲师, 主要从事有机合成研究. E-mail: wkpwkp469@sina.com

Synthesis of Benzimidazole Derivatives in Water Under Imidazolium Salt Grafted Iodobenzene Diacetate Assisted

WANG Xiao-Ke, TIAN Mi*

College of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, China

Received:2009-04-09 Online:2010-02-10 Published:2010-02-10
Contact: TIAN Mi. E-mail: wkpwkp469@sina.com

摘要/Abstract

摘要：

报道了一种简便高效的苯并咪唑类衍生物的水相合成新方法, 合成了兼具离子液体和二醋酸碘苯双重特点的咪唑盐二醋酸碘苯. 以水为溶剂, 在咪唑盐二醋酸碘苯促进下, 通过邻苯二胺或4-甲基邻苯二胺与各种芳醛室温氧化环合, 一步合成了13种苯并咪唑类衍生物, 反应时间25～45 min, 反应产率92％～98％. 用核磁共振、红外光谱、质谱和元素分析对产物的结构进行了表征, 提出了可能的反应机理. 该合成方法具有底物适用范围广、反应条件温和、反应速度快、反应产率高及氧化剂对应的还原产物可回收利用等优点, 是一种环境友好的绿色合成方法.

关键词: 咪唑盐二醋酸碘苯; 邻苯二胺; 芳醛; 绿色合成; 苯并咪唑类衍生物

Abstract:

We developed a simple and efficient method for the synthesis of benzimidazole derivatives in water. Imidazolium salt grafted iodobenzene diacetate containing double features of ionic liquid and iodobenzene diacetate was synthesized. Thirteen benzimidazole derivatives were synthesized by one-step oxidative cyclisation of 1,2-phenylenediamine or 4-methyl-1,2-phenylenediamine at room temperature and a series of aromatic aldehydes under imidazolium salt grafted iodobenzene diacetate assisted. The reactions were completed in 25—45 min with 92％—98％ yields. The structure of products were characterized by ¹H NMR and IR, MS spectra and elemental analysis. The synthetic method has such advantages as the broad scope of application of reactants, mild reaction conditions, faster reaction velocity, reasonably good yields, high efficient recycling oxidants and environmental benign. In addition, the possible mechanism of the reaction was proposed.

Key words: Imidazolium salt grafted iodobenzene diacetate; 1,2-Phenylenediamine; Aromatic aldehyde; Green synthesis; Benzimidazole derivative

TrendMD:

王孝科, 田敉. 咪唑盐二醋酸碘苯促进苯并咪唑类衍生物的水相合成. 高等学校化学学报, 2010, 31(2): 296.

WANG Xiao-Ke, TIAN Mi*. Synthesis of Benzimidazole Derivatives in Water Under Imidazolium Salt Grafted Iodobenzene Diacetate Assisted. Chem. J. Chinese Universities, 2010, 31(2): 296.

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