有机化学 ›› 2018, Vol. 38 ›› Issue (8): 2130-2136.DOI: 10.6023/cjoc201802027 上一篇    下一篇

研究简报

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   

  1. 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 Kanga, Gu Huiwena, Zhang Fangb, Xu Xiaojuanb, Zhang Lijied, Sun Yaquanb,c   

  1. 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).

研究了1,2,6-三取代苯并咪唑衍生物合成的新方法.即以3-氟-4-硝基苄腈和芳香胺为初始原料,借助微波合成中间体N-取代-2-硝基-4-腈基苯胺(1),在Na2S2O4作用下,化合物1与不同的醛反应,一步关环合成1,2,6-三取代苯并咪唑衍生物.第一步反应微波技术的使用,大大缩短了反应时间,提高了产率.通过优化,第二步反应最优实验条件为:以二甲基亚砜(DMSO)-H2O为溶剂,n(中间体):n(对氯苯甲醛):n(保险粉)=1:1:9,在80℃下反应2 h.应用该方法,合成21个1,2,6-三取代苯并咪唑衍生物.

关键词: 合成, 苯并咪唑, 工艺优化, 一锅法

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