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2023 , Vol. 43 >Issue 9: 3180 - 3187

DOI: https://doi.org/10.6023/cjoc202303031

研究论文

偶氮次甲基亚胺与氮杂二烯前体的[4+3]环加成反应构建功能化四氮杂䓬衍生物

  • 张晓轲 ,
  • 郑相如 ,
  • 王朝永
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  • a 重庆大学附属涪陵医院中心实验室 重庆 408000
    b 重庆医科大学附属第三医院 重庆 401120
    c 遵义医科大学 贵州 563006

收稿日期: 2023-03-21

  修回日期: 2023-05-15

  网络出版日期: 2023-06-07

基金资助

贵州省科技厅基础研究计划(QKHJC-ZK[2023]-495); 重庆市自然科学基金(cstc2021jcyj-bsh0010)

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Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

  • Xiaoke Zhang ,
  • Xiangru Zheng ,
  • Chaoyong Wang
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  • a Central Laboratory, Chongqing University Fuling Hospital, Chongqing 408000
    b The Third Affiliated Hospital of Chongqing Medical University, Chongqing 401120
    c Zunyi Medical University, Guizhou 563006
* E-mail: ;
* E-mail: ;

Received date: 2023-03-21

  Revised date: 2023-05-15

  Online published: 2023-06-07

Supported by

Guizhou Provincial Science and Technology Plan Program(QKHJC-ZK[2023]-495); Chongqing Natural Science Foundation(cstc2021jcyj-bsh0010)

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摘要

四氮杂䓬衍生物具有良好的生物活性, 目前, 对于该骨架的构建方法非常有限, 因此, 建立了一种通过氢氧化钾促进α-卤代乙酰腙原位形成1,2-氮杂二烯中间体, 与偶氮次甲基亚胺环合反应合成高度取代的四氮杂䓬衍生物的新方法. 该方法表现出良好的官能团耐受性和底物普适性.

关键词： α-卤代乙酰腙; 偶氮次甲基亚胺; 四氮杂䓬衍生物; 氮杂二烯前体

本文引用格式

张晓轲 , 郑相如 , 王朝永 . 偶氮次甲基亚胺与氮杂二烯前体的[4+3]环加成反应构建功能化四氮杂䓬衍生物[J]. 有机化学, 2023 , 43(9) : 3180 -3187 . DOI: 10.6023/cjoc202303031

Abstract

Tetrazepine derivative exhibits good biological activities. Only a limited method has been devoted to constructing these frameworks to date. Therefore, an efficient and novel way was established for the synthesis of functionalized tetrazepine scaffolds through the cycloaddition reaction of azomethine imine with 1,2-azadiene formed in situ by α-halogeno hydrazones in the presence of KOH. This transformation shows excellent functional group tolerance and substrate scope.

Key words： α-halogeno hydrazone; azomethine imine; tetrazepine derivative; azadiene precursor

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