Synthesis of 1,2,6-Trisubstituted Benzimidazoles

doi:10.6023/cjoc201802027

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2130-2136.DOI: 10.6023/cjoc201802027 Previous Articles Next Articles

Notes

1,2,6-三取代苯并咪唑的合成研究

杨康^a, 顾惠雯^a, 张芳^b, 许晓娟^b, 张立洁^d, 孙雅泉^b,c

a 南京工业大学化工学院南京 210000;
b 盐城师范学院药学院盐城 224002;
c 江苏海洋产业研究院盐城 224100;
d 盐城通达药业有限公司盐城 224100

收稿日期:2018-02-28 修回日期:2018-05-05 发布日期:2018-05-24
通讯作者: 孙雅泉 E-mail:sunyaquan@hotmail.com
基金资助:
江苏省前瞻科研（No.BY2016066-02）资助项目.

Synthesis of 1,2,6-Trisubstituted Benzimidazoles

Yang Kang^a, Gu Huiwen^a, Zhang Fang^b, Xu Xiaojuan^b, Zhang Lijie^d, Sun Yaquan^b,c

a School of Chemical Engineering, Nanjing TECH University, Nanjing 210000;
b School of Pharmacy, Yancheng Teachers University, Yancheng 224002;
c Jiangsu Marine Industry Research Institute, Yancheng 224100;
d Yancheng Tongda Pharmaceutical Co., Ltd., Yancheng 224100

Received:2018-02-28 Revised:2018-05-05 Published:2018-05-24
Contact: 10.6023/cjoc201802027 E-mail:sunyaquan@hotmail.com
Supported by:
Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02).

1. Synthesis of 1,2,6-Trisubstituted Benzimidazoles.PDF(8954KB)

Abstract

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

Cite this article

Yang Kang, Gu Huiwen, Zhang Fang, Xu Xiaojuan, Zhang Lijie, Sun Yaquan. Synthesis of 1,2,6-Trisubstituted Benzimidazoles[J]. Chin. J. Org. Chem., 2018, 38(8): 2130-2136.

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1,2,6-三取代苯并咪唑的合成研究

Synthesis of 1,2,6-Trisubstituted Benzimidazoles

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