Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2506-2518.DOI: 10.6023/cjoc202211009 Previous Articles     Next Articles

ARTICLES

青藤碱N-四氮唑和N-噁二唑杂环衍生物的设计与合成

武学丹, 徐瑞祥, 方霄龙, 张克华, 金杰*()   

  1. 安徽建筑大学材料与化学工程学院 功能分子设计与界面过程重点实验室 合肥 230601
  • 收稿日期:2022-11-08 修回日期:2023-01-25 发布日期:2023-02-14
  • 通讯作者: 金杰
  • 基金资助:
    安徽建筑大学科研启动基金(2020QDZ03); 及安徽建筑大学基金(JZ202219); 及安徽建筑大学基金(JZ202249)

Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine

Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin()   

  1. Key Laboratory of Functional Molecule Design and Interface Process, College of Materials and Chemical Engineering, Anhui Jianzhu University, Hefei 230601
  • Received:2022-11-08 Revised:2023-01-25 Published:2023-02-14
  • Contact: Jie Jin
  • Supported by:
    Starting Grants of Anhui Jianzhu University(2020QDZ03); Foundation of Anhui Jianzhu University(JZ202219); Foundation of Anhui Jianzhu University(JZ202249)

Two new synthesis methods were established, N-tetrazole and N-1,3,4-oxadiazole substituted heterocyclic derivatives of sinomenine were constructed on the N atom of D-ring, and 34 new sinomenine heterocyclic derivatives were synthesized. N-CN sinomenine at 17-position was generated by substituted reaction between cyanogen bromide and sinomenine, and then N-tetrazole sinomenine was achieved by 1,3-dipolar cycloaddition reaction with NaN3. The reaction of tetrazole with benzyl chloride produced N-tetrazole heterocyclic derivatives of sinomenine. N-1,3,4-Oxadiazole heterocyclic derivatives of sinomenine were obtained by acylation reaction and the Huisigen rearrangement reaction of tetrazole with acyl chloride reagents. These methods with mild condition gave good to excellent yields. This method provides new methods for structural modification of natural products, the synthesized compounds expand the library of sinomenine derivatives, and this work provides a basis study for drug molecular design and potential activity study.

Key words: sinomenine, tetrazole, oxadiazole, derivative