Chinese Journal of Organic Chemistry >
Synthesis of 1,2,6-Trisubstituted Benzimidazoles
Received date: 2018-02-28
Revised date: 2018-05-05
Online published: 2018-05-24
Supported by
Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02).
A novel synthetic method for 1,2,6-trisubstituted benzimidazole derivatives was developed, which started from 3-fluoro-4-nitrobenzonitrile and aromatic amines to give the intermediates N-substituted-2-nitro-4-cyanoaniline (1) with high yield and short reaction time under microwave irradiation condition. Then, compound 1 reacted with different aldehydes in the presence of Na2S2O4 to provide the final compounds. Meanwhile, the process of the reactions was optimized in this study and the optimized conditions are described as:dimethyl sulfoxide (DMSO)-H2O as solvent, n(compound 1):n(4-chlorobenzaldehyde):n(sodium dithionite)=1:1:9 at 80℃ for 2 h. Employing the same synthetic method, 21 1,2,6-trisubstituted benzimidazole derivatives were synthesized.
Key words： synthesis; benzimidazole; process optimization; one-pot reaction
Yang Kang , Gu Huiwen , Zhang Fang , Xu Xiaojuan , Zhang Lijie , Sun Yaquan . Synthesis of 1,2,6-Trisubstituted Benzimidazoles[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 2130 -2136 . DOI: 10.6023/cjoc201802027
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