Citation: 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]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 165-171. doi: 10.6023/cjoc201507010 shu

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

1.
College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094

Corresponding author: Lu Ming, luming@mail.njust.edu.cn
Received Date: 14 July 2015
Revised Date: 10 September 2015

Fund Project: the National Natural Science Foundation of China 51374131

Figures(2)

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