Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Azomethine Imines with Electron-Deficient Alkenes: A Facile Access to Dinitrogen-Fused Heterocycles

被引:52
|
作者
Li, Zhen [1 ]
Yu, Hao [1 ]
Liu, Honglei [1 ]
Zhang, Lei [1 ]
Jiang, Hui [1 ]
Wang, Bo [1 ]
Guo, Hongchao [1 ]
机构
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
alkenes; azomethine imine; catalysis; cycloaddition reactions; phosphine; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ALLENES; ANNULATIONS; ALLENOATES; ALKYNES;
D O I
10.1002/chem.201303625
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for the phosphine-catalyzed [3+2] cycloaddition reaction of azomethine imines with diphenylsulfonyl alkenes to give dinitrogen-fused bi- or tricyclic heterocyclic compounds in high yields has been described. Moreover, two phenylsulfonyl groups installed on the heterocyclic products could be conveniently removed or transformed to other functional groups, making the reaction more useful.
引用
收藏
页码:1731 / 1736
页数:6
相关论文
共 50 条
  • [1] DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: facile access to dinitrogen-fused heterocycles
    Jia, Qianfa
    Chen, Lei
    Yang, Gongming
    Wang, Jian
    Wei, Jia
    Du, Zhiyun
    [J]. TETRAHEDRON LETTERS, 2015, 56 (52) : 7150 - 7153
  • [2] Thermal [3+2] cycloaddition reaction of azomethine imines with allenoates for dinitrogen-fused heterocycles
    Na, Risong
    Liu, Honglei
    Li, Zhen
    Wang, Bo
    Liu, Jun
    Wang, Ming-An
    Wang, Min
    Zhong, Jiangchun
    Guo, Hongchao
    [J]. TETRAHEDRON, 2012, 68 (10) : 2349 - 2356
  • [3] Mechanism, regioselectivity, and the kinetics of phosphine-catalyzed [3+2] cycloaddition reactions of allenoates and electron-deficient alkenes
    Liang, Yong
    Liu, Song
    Xia, Yuanzhi
    Li, Yahong
    Yu, Zhi-Xiang
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (14) : 4361 - 4373
  • [4] Phosphine-catalyzed highly diastereoselective [3+2] cyclization of isatin derived electron-deficient alkenes with α-allenic esters
    Zhang, Xiu-Chun
    Cao, Shu-Hua
    Wei, Yin
    Shi, Min
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (05) : 1548 - 1550
  • [5] Synthesis of novel unique pyrrolidines by [3+2]-cycloaddition of azomethine ylides with electron-deficient alkenes
    Yavnyik, Iryna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [6] Asymmetric Dearomatization of Electron-Deficient Heteroarenes by a Phosphine-Catalyzed [3+2] Annulation with Vinylcyclopropanes
    Dai, Xuan
    Zhang, Fuhao
    Dai, Lei
    Lu, Yixin
    [J]. CCS CHEMISTRY, 2023, 5 (09): : 2023 - 2032
  • [7] Synthesis of novel unique pyrrolidines by [3+2]-cycloaddition of azomethine ylides with electron-deficient alkenes
    Mykhailiuk, Pavel
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [8] A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates
    Wang, De
    Lei, Yu
    Wei, Yin
    Shi, Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (47) : 15325 - 15329
  • [9] Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes
    Gao, Wenzhong
    Raghunath, Malati
    Zhang, Xumu
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3060 - U3060
  • [10] Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles
    Mao, Biming
    Xu, Yi
    Chen, Yuehua
    Dong, Jipan
    Zhang, Junya
    Gu, Kejia
    Zheng, Bing
    Guo, Hongchao
    [J]. ORGANIC LETTERS, 2019, 21 (12) : 4424 - 4427