有机化学 ›› 2013, Vol. 33 ›› Issue (03): 615-620.DOI: 10.6023/cjoc201210037 上一篇    下一篇

研究论文

无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮(艹卓)-2(3H)-酮的简易合成

翟士燕a, 曹卫国a,b,c, 张慧a   

  1. a 上海大学化学系 上海 200444;
    b 中国科学院上海有机化学研究所金属有机国家重点开放实验室 上海 200032;
    c 中国科学院上海有机化学研究所氟化学重点开放实验室 上海 200032
  • 收稿日期:2012-10-19 修回日期:2012-11-18 发布日期:2012-11-23
  • 通讯作者: 张慧 E-mail:yehao7171@shu.edu.cn; wgcao@staff.shu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21072126, 21272152)、上海市教育委员会重点学科建设资金(No. J50102)资助项目.

Facile Synthesis of Perfluoroalkyl Substituted 1H-Benzo[b][1,4]- diazepine-2(3H)-ones via a Catalyst-Free Process

Zhai Shiyana, Cao Weiguoa,b,c, Zhang Huia   

  1. a Department of Chemistry, Shanghai University, Shanghai 200444;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2012-10-19 Revised:2012-11-18 Published:2012-11-23
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21072126, 21272152) and the Leading Academic Discipline Projects of Shanghai Municipal Education Commission (No. J50102).

1,5-苯并二氮(艹卓)-2-酮作为一个独特的骨架广泛存在于很多具有生理活性的化合物中, 而全氟烷基的引入影响到有机化合物的理化性质以及生理活性的改变. 因此将全氟代烷基引入1,5-苯并二氮(艹卓)-2-酮的方法的研究正变得日趋重要. 发展了一个制备全氟代烷基取代的1,5-苯并二氮(艹卓)-2-酮的简易方法. 采用全氟代炔酸甲酯为含氟砌块, 与邻芳基二胺, 以无水甲苯为溶剂, 在无催化剂存在条件下, 80 ℃反应24 h, 以较好的收率顺利得到4-全氟烷基-1,3-二氢-1,5-苯并二氮(艹卓)-2-酮类化合物.

关键词: 全氟烷基, 1,5-苯并二氮(艹卓)-2-酮, 全氟烷基炔酸甲酯, 邻芳基二胺

1,5-Benzodiazepin-2-one is a privileged scaffold and compounds containing such substructures exhibit a range of biological activities. Perfluoroalkyl groups can favorably affect the physical and biological properties of organic compounds. Accordingly, the development of methods to introduce perfluoroalkyl groups into 1,5-benzodiazepin-2-ones has become increasingly important. Herein, an efficient and simple route for preparation of perfluoroalkylated 1,5-benzodiazepine-2-ones is described. The reaction of methyl 3-perfluoroalkyl-2-alkynoate as the fluorinated building block with o-arylenediamine proceeds smoothly in dry toluene at 80 ℃ for 24 h without any catalyst to afford the titled compounds in good yields.

Key words: perfluoroalkyl, 1,5-benzodiazepine-2-one, methyl 3-perfluoroalkyl-2-alkynoate, o-arylenediamine