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2022 , Vol. 42 >Issue 1: 190 - 199

DOI: https://doi.org/10.6023/cjoc202107018

研究论文

基于非对称性三唑萘啶吡啶铜催化合成吡嗪与酮衍生物

  • 李家豪 ,
  • 杨义科 ,
  • 胡文康 ,
  • 夏晓峰 ,
  • 王大伟
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  • a 江南大学化学与材料工程学院 教育部合成与生物胶体重点实验室 江苏无锡 214122
    b 河南警察学院刑事科学技术系 郑州 450046

收稿日期: 2021-07-07

  修回日期: 2021-09-02

  网络出版日期: 2021-09-08

基金资助

国家自然科学基金(21776111)

收起

Catalytic Synthesis of Pyrazine and Ketone Derivatives by Unsymmetrical Triazolyl-Naphthyridinyl-Pyridine Copper

  • Jiahao Li ,
  • Yike Yang ,
  • Wenkang Hu ,
  • Xiaofeng Xia ,
  • Dawei Wang
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  • a Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122
    b Department of Criminal Science and Technology, Henan Police College, Zhengzhou 450046
* Corresponding author. E-mail:

Received date: 2021-07-07

  Revised date: 2021-09-02

  Online published: 2021-09-08

Supported by

National Natural Science Foundation of China(21776111)

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摘要

发展了一种基于非对称性配体的催化剂TNP-Cu@rGO, 并将该催化剂用于催化合成吡嗪和酮衍生物的新方法. 对该反应中碱的种类、溶剂、反应温度和时间等条件进行了优化, 确定了最优的反应条件. 接着对该反应的底物普适性进行了研究, 实验表明该催化体系显示了良好的官能团耐受性, 并对该催化体系和反应进行了机理研究和探索. 催化剂的回收循环再利用实验表明, 该催化剂循环使用五次仍能保持较高的催化活性.

关键词： 借氢; 非对称性; 吡嗪; 铜

本文引用格式

李家豪 , 杨义科 , 胡文康 , 夏晓峰 , 王大伟 . 基于非对称性三唑萘啶吡啶铜催化合成吡嗪与酮衍生物[J]. 有机化学, 2022 , 42(1) : 190 -199 . DOI: 10.6023/cjoc202107018

Abstract

A novel method for the synthesis of pyrazine and ketone derivatives was developed by using asymmetric ligand-based catalyst TNP-Cu@rGO. The screening of reaction bases, solvents, reaction temperatures and time was conducted to determine optimal reaction conditions. The reaction scope and generality of this methodology for the synthesis of pyrazines were tested and the results showed that this catalytic system had good functional tolerance. More than twenty substrates experiments were successfully set up, and pyrazines with moderate to high yields were isolated. Additionally, this catalytic system could also be used to the systhesis of ketones in good yields. Furthermore, the mechanism investigations were conducted for the synthesis of pyrazine derivatives to better understand the synthesis of pyrazines. The recycling test of TNP-Cu@rGO for the synthesis of pyrazines was investigated and the experiments showed that the catalyst could still maintain high catalytic activity for five times.

Key words： borrowing hydrogen; unsymmetrical; pyrazine; copper

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