有机化学 ›› 2018, Vol. 38 ›› Issue (4): 791-801.DOI: 10.6023/cjoc201709025 上一篇    下一篇

所属专题: 元素有机化学合辑2018-2019

综述与进展

α-芳基烯基叠氮参与的含氮杂环化合物合成研究进展

严珺a, 姬晓悦b, 花书贵a, 王静a   

  1. a 江苏第二师范学院生命科学与化学化工学院 江苏省生物功能分子重点建设实验室 南京 210013;
    b 南京林业大学现代分析测试中心 南京 210037
  • 收稿日期:2017-09-15 修回日期:2017-10-13 发布日期:2017-11-15
  • 通讯作者: 花书贵 E-mail:huashugui@jssnu.edu.cn
  • 基金资助:

    江苏省自然科学基金(No.BK20130748)资助项目.

Recent Advances of α-Aryl Vinyl Azides in Nitrogen Heterocycle Synthesis

Yan Juna, Ji Xiaoyueb, Hua Shuguia, Wang Jinga   

  1. a Key Construction Laboratory of Bio-functional Molecular of Jiangsu Province, Life Science and Chemistry College, Jiangsu Second Normal University, Nanjing 210013;
    b Advanced Analysis & Testing Center, Nanjing Forestry University, Nanjing 210037
  • Received:2017-09-15 Revised:2017-10-13 Published:2017-11-15
  • Contact: 10.6023/cjoc201709025 E-mail:huashugui@jssnu.edu.cn
  • Supported by:

    Project supported by the Natural Science Foundation of Jiangsu Province (No. BK20130748).

含氮杂环化合物广泛存在于天然产物、药物化学和材料化学中.α-芳基烯基叠氮因其结构中烯烃与叠氮相连而具有独特的性质,能够充当亲电试剂、亲核试剂或自由基接受体.此外,能通过多样的反应途径生成高反应活性的中间体,为发展新颖的反应提供了可能.近年来,越来越多的化学家们利用α-芳基烯基叠氮作为关键的三原子合成子构建了各种结构复杂的含氮杂环化合物.系统地介绍近年来利用α-芳基烯基叠氮制备各种N-杂环化合物的进展,总结归纳各反应机理、反应特点和应用研究,为合成含氮杂环化合物的研究提供帮助.

关键词: α-芳基烯基叠氮, 合成子, 氮杂环化合物, 应用研究

Nitrogen heterocyclic compounds can be found in various natural products, pharmaceutical chemistry and material chemistry. Due to azide group linked to olefins, α-aryl vinyl azide has unique properties, which can act as electrophilic reagents, nucleophilic reagent, or radical acceptor. Diverse reaction pathways of α-aryl vinyl azide provide great opportunities to generate highly reactive intermediates with unusual or unconventional reactivities, making it possible to develop novel reaction. Recently, more and more synthetic chemists used α-aryl vinyl azide as a key three atoms synthon for the construction of diverse structurally complex N-heterocyclic compounds. This review will introduce systematically the reactivities of α-aryl vinyl azide and the developments of the recent application of α-aryl vinyl azide in nitrogen heterocycle synthesis, including mechanism, reaction characteristics and application study, thus it may be helpful for the research on nitrogen heterocycle synthesis.

Key words: α-aryl vinyl azide, synthon, nitrogen heterocyclic compounds, application