有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3132-3153.DOI: 10.6023/cjoc202005092 上一篇    下一篇

综述与进展

1,3-偶极子[3+n](n≥3)环加成反应的研究进展

乐贵洲a, 刘波b   

  1. a 四川农业大学理学院 四川雅安 625014;
    b 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064
  • 收稿日期:2020-05-30 修回日期:2020-06-19 发布日期:2020-07-01
  • 通讯作者: 乐贵洲 E-mail:yueguizhou@sicau.edu.cn;chembliu@scu.edu.cn
  • 基金资助:
    四川省科技计划(No.2020YFH0129)资助项目.

Research Progress on [3+n] (n≥3) Cycloaddition of 1,3-Diploes

Yue Guizhoua, Liu Bob   

  1. a School of Science, Sichuan Agricultural University, Ya'an, Sichuan 625014;
    b Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064
  • Received:2020-05-30 Revised:2020-06-19 Published:2020-07-01
  • Supported by:
    Project supported by the Science and Technology Program of Sichuan Province (No. 2020YFH0129).

各种杂环骨架广泛存在于天然产物、药物分子及有机材料中,它们的合成方法也多种多样,其中1,3-偶极环加成反应是构建杂环重要的一类方法.2005年之前,有机化学家们将精力主要集中在1,3-偶极子的[3+2]环加成反应,构建五元杂环;随着研究的深入,逐渐将注意力转向[3+3]、[3+4]、[3+5]及[3+6]等环加成,构建六元、七元、八元及桥杂环等.关于1,3-偶极环加成反应的综述已有很多,但它们讨论的重点是[3+2]环加成.到目前为止,还没有专门的综述来探讨其它环加成反应的概况及其应用前景.因此,对各种1,3-偶极子的[3+n](n≥3)环加成反应进行详细的综述及评论,并对其领域提出展望.

关键词: 1,3-偶极环加成, 硝酮, 亚甲胺叶立德, 偶氮次甲基亚胺, 氰基亚胺, 氰基氧化物, 氰基叶立德

Versatile heterocyclic skeletons extensively exist in structures of natural products, drug molecules and organic materials, and have been synthesized through various strategies reported in literatures. Among them, the 1,3-dipolar cycloaddition is the most impressive class to build the related heterocycles. In the past, organic chemists generally employed[3+2] cycloaddition of 1,3-dipoles to assemble five-membered rings. As modern chemistry developes, researchers further turn their attention to the[3+3],[3+4],[3+5] and[3+6] cycloadditions, to construct six-, seven-, eight- and bridge-heterocyclic compounds. At present, review articles with topics on 1,3-dipolar cycloaddition mainly focus on[3+2] cycloaddition. Herein, A topic on[3+n] (n ≥ 3) cycloaddition of 1,3-dipoles, with comments on the developed methodologies is present and the outlook in this field is proposed.

Key words: 1,3-diploar cycloaddtion, nitrone, azomethine ylide, azomethine imine, nitrile imine, nitrile oxide, nitrile ylide