研究简报

铁粉促进“一锅法”合成1-苯基苯并咪唑类化合物

  • 余祖滔 ,
  • 王泽瑜 ,
  • 吴肖 ,
  • 胡高云 ,
  • 李乾斌
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  • a. 中南大学药学院药物化学系 长沙 410013;
    b. 湖南师范大学医学院药学 长沙 410013

收稿日期: 2015-12-03

  修回日期: 2016-03-10

  网络出版日期: 2016-03-25

基金资助

国家自然科学基金(No.21102184)和高等学校博士学科点专项科研基金(No.20110162120033)资助项目.

“One-Pot” Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe

  • Yu Zutao ,
  • Wang Zeyu ,
  • Wu Xiao ,
  • Hu Gaoyun ,
  • Li Qianbin
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  • a. Medicinal Chemistry of Pharmacy Department, Central South University, Changsha 410013;
    b. Medicine Department, Hunan Normal University, Changsha 410013

Received date: 2015-12-03

  Revised date: 2016-03-10

  Online published: 2016-03-25

Supported by

Project supported by the the National Natural Science Foundation of China (No. 21102184) and the Specialized Research Fund for the Doctoral Program of Higher Education of China (No. 20110162120033).

摘要

成功开发了由铁粉促进“一锅法”合成1-苯基苯并咪唑类化合物的简易合成方法. 以取代邻硝基二苯胺为原料,液体有机酸为溶剂,在铁粉作用下还原并直接环合生成1-苯基-苯并咪唑类化合物,产率80%~93%. 通过高效液相色谱(HPLC)监测分析反应进程,探讨反应的机理,并确定了最佳反应条件. 该合成方法条件温和,操作简单,原料易得,产率较高,为该类化合物的合成提供了一种新的便利方法.

本文引用格式

余祖滔 , 王泽瑜 , 吴肖 , 胡高云 , 李乾斌 . 铁粉促进“一锅法”合成1-苯基苯并咪唑类化合物[J]. 有机化学, 2016 , 36(7) : 1672 -1676 . DOI: 10.6023/cjoc201512007

Abstract

An easy and efficient “one-pot” synthetic method facilitated by Fe to synthesize substituted 1-phenyl-1H-benzimi- dazole has been developed successfully. By using liquid organic acid as solvent, 2-nitro-N-phenylaniline is converted to substituted 1-phenyl-1H-benzimidazole directly after reduction and cyclization catalyzed by Fe, with the yield of 80%~92%. Through the application of high performance liquid chromatography (HPLC) detection, the effects of the amount of solvent, the type of liquid organic acid, temperature and reaction time on the “one-pot” reaction have been fully investigated, as well as the reaction mechanism. The “one-pot” method proposed here has multiple advantages, such as mild condition, easy procedure, cheap ingredients and high yield, which provide a newly convenient synthetic route.

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