Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 160-171.DOI: 10.6023/cjoc202106028 Previous Articles     Next Articles



王明亮, 尹刘燕, 温甜甜, 张晓, 高杰, 王兰芝*()   

  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:2021-06-17 修回日期:2021-09-03 发布日期:2021-09-26
  • 通讯作者: 王兰芝
  • 基金资助:

Green Synthesis of 1,5-Benzodiazepines with Multifunctional Groups

Mingliang Wang, Liuyan Yin, Tiantian Wen, Xiao Zhang, Jie Gao, Lanzhi Wang()   

  1. College of Chemistry & Materials Science, Hebei Normal University, Key Laboratory of Organic Functional Molecules of Hebei Province, Shijiazhuang 050024
  • Received:2021-06-17 Revised:2021-09-03 Published:2021-09-26
  • Contact: Lanzhi Wang
  • Supported by:
    National Natural Science Foundation of China(21776060)

1,5-Benzodiazepine compounds are seven-membered nitrogen heterocyclic compounds with important biological and pharmacological activities. Ester group, carboxyl group, acyl group and aryl group are active groups of 1,5-benzodiazepine compounds. One-pot green synthesis of 34 kinds of 1,5-benzodiazepines with COR, COOR or COOH by three-component tandem reaction was performed at room temperature (25 ℃) with a yield of up to 90%. The mechanism of catalytic tandem reaction was proposed. These reactions were achieved by using aldehyde carbonyl compounds or dicarbonyl compounds, 3-butyn-2-one, substituted o-phenylenediamine as raw materials, absolute ethanol as solvent, magnetic nano cobalt ferrite (CoFe2O4) was realized under catalyst or without catalyst. The multifunctional 1,5-benzodiazepine compounds were formed via Michael addition reaction, nucleophilic addition-dehydration reaction, intramolecular imine-enamine cyclization and proton transfer processes, which realized that multiple active groups such as active acyl, ester or carboxyl groups were simultaneously introduced into the seven-membered ring of the benzodiazepine in a reaction system under mild conditions. This synthesis method has the advantages of novel synthesis method, atom economy, high yield and selectivity of the target compounds, which realize the green reaction process, and provide a new idea for green synthesis of benzozazepines.

Key words: three-component tandem reaction, green synthesis, 1,5-benzodiazepine compounds