有机化学 ›› 2016, Vol. 36 ›› Issue (1): 165-171.DOI: 10.6023/cjoc201507010 上一篇    下一篇

研究论文

铁(III)催化亚胺和邻苯二胺的有氧氧化合成苯并咪唑的研究

赵丹丹, 虞家涛, 王鹏程, 陆明   

  1. 南京理工大学化工学院 江苏 南京 210094
  • 收稿日期:2015-07-14 修回日期:2015-09-10 出版日期:2016-01-25 发布日期:2015-09-17
  • 通讯作者: 陆明 E-mail:luming@mail.njust.edu.cn
  • 基金资助:

    国家自然科学基金(No. 51374131)资助项目.

Aerobic Oxidation Synthesis of Benzimidazoles via Iron(III)-Catalyzed the Reaction of Imine Derivatives with o-Phenylenediamine

Zhao Dandan, Yu Jiatao, Wang Pengcheng, Lu Ming   

  1. College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094
  • Received:2015-07-14 Revised:2015-09-10 Online:2016-01-25 Published:2015-09-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 51374131).

详细探究了铁催化氧化亚胺和邻苯二胺生成苯并咪唑的合成反应. 该反应过程可分为三步: 第一步是亚胺和邻苯二胺氧化缩合生成席夫碱, 第二步是席夫碱与邻苯二胺上另一氨基亲核加成生成苯并咪唑啉, 第三步苯并咪唑啉氧化脱氢生成目标产物苯并咪唑. 结果表明, 以Fe(NO3)3·9H2O为催化剂, 乙腈为溶剂, 在80 ℃下反应10 h可以获得良好收率. 而且这种方法以经济、绿色的空气作为氧化剂, 具有良好的应用前景.

关键词: 苯并咪唑衍生物, 合成, Fe(NO3)3·, 9H2O, 亚胺, 邻苯二胺

In this paper, Iron(III)-catalyzed aerobic oxidation of imine derivatives and o-phenylenediamine under air condition is studied in detail. With Fe(NO3)3·9H2O as catalyst and air as green and economical oxidant, the reaction could take place in acetonitrile at 80 ℃ and affords benzimidazoles as target compounds in good yields after 10 h, exhibiting good application prospect as well. This process includes three steps: (1) the aerobic oxidative condensation of imine and o-phenylenediamine to form Schiff base, (2) the formation of benzimidazoline via nucleophilic addition of Shift base and amine group on the o-phenylenediamine, and (3) the dehydration of benzimidazoline to form benzimidazole as target compounds.

Key words: benzimidazoles, synthesis, Fe(NO3)3·, 9H2O, imine derivatives, o-phenylenediamine