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

doi:10.6023/cjoc201507010

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (1): 165-171.DOI: 10.6023/cjoc201507010 Previous Articles Next Articles

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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

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 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

College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094

Received:2015-07-14 Revised:2015-09-10 Published:2015-09-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51374131).

1. Aerobic Oxidation Synthesis of Benzimidazoles via Iron(III)-Catalyzed the Reaction of Imine Derivatives with o-Phenylenediamine.PDF(934KB)

Abstract

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

Cite this article

Zhao Dandan, Yu Jiatao, Wang Pengcheng, Lu Ming. Aerobic Oxidation Synthesis of Benzimidazoles via Iron(III)-Catalyzed the Reaction of Imine Derivatives with o-Phenylenediamine[J]. Chin. J. Org. Chem., 2016, 36(1): 165-171.

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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

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

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