Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 806-818.DOI: 10.6023/cjoc202006040 Previous Articles     Next Articles



李静1, 郝振芳1, 张凯悦1, 王兰芝1,*()   

  1. 1 河北师范大学化学与材料科学学院 河北省有机功能分子重点实验室 石家庄 050024
  • 收稿日期:2020-06-20 修回日期:2020-09-03 发布日期:2020-10-15
  • 通讯作者: 王兰芝
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    国家自然科学基金(21776060); 河北省自然科学基金(B2016205165)

One-Pot Synthesis of 1,5-Benzodiazepine Compounds by Three-Component Tadem Reaction

Jing Li1, Zhenfang Hao1, Kaiyue Zhang1, Lanzhi Wang1,*()   

  1. 1 Laboratory of Organic Functional Molecules of Hebei Province, College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang, Hebei 050024
  • Received:2020-06-20 Revised:2020-09-03 Published:2020-10-15
  • Contact: Lanzhi Wang
  • Supported by:
    the National Natural Science Foundation of China(21776060); the Natural Science Foundation of Hebei Province(B2016205165)

43 novel 1,5-benzodiazepine compounds were obtained via one-pot multicomponent and tadem reactions for 2~5 h and the yield of the target compounds is up to 95%. These reactions were achieved by reacting substituted 1,2-phenylene- diamines, 1,3-cyclopentanedione or 1,3-cyclohexanedione (5,5-dimethyl-1,3-cyclohexanedione), 2,3-dicarbonyl compounds with p-toluenesulfonic acid as catalyst in EtOH. The active intermediates with the imine and enamine structures in the molecule were formed by two nucleophilic addition-dehydration processes and then 1,5-benzodiazepine compounds were obtained via carbon-carbon coupling cyclization and proton transfer processes, which realized the construction of one new seven- membered ring and four new chemical bonds (two C—N, one C=C, one C—C) in one-pot. It provides a green, environmentally friendly, efficient and simple synthetic thought for the synthesis of 1,5-benzodiazepine compounds.

Key words: 1,5-benzodiazepine compound, tadem reaction, green synthesis, mechanism