Chinese Journal of Organic Chemistry >
Aerobic Oxidation Synthesis of Benzimidazoles via Iron(III)-Catalyzed the Reaction of Imine Derivatives with o-Phenylenediamine
Received date: 2015-07-14
Revised date: 2015-09-10
Online published: 2015-09-17
Supported by
Project supported by the National Natural Science Foundation of China (No. 51374131).
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
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, 2016 , 36(1) : 165 -171 . DOI: 10.6023/cjoc201507010
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