Synthesis of Chlorin-Fused Monospirooxindolopyrrolidines Through a Facile [3+2]-Cycloaddition of Azomethine Ylides

被引:8
|
作者
Saravanan, P. [1 ]
Babu, A. R. Suresh [1 ]
Raghunathan, R. [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras, Tamil Nadu, India
关键词
Azomethine ylide; cycloaddition; oxindolopyrrolidines; porphyrin; spiroheterocycles; 1,3-DIPOLAR CYCLOADDITION REACTIONS; PHOTOINDUCED ELECTRON-TRANSFER; PORPHYRINS;
D O I
10.1080/00397910903243799
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot synthesis of novel chlorin-fused monospirooxindolopyrrolidines has been accomplished in good yield via a facile [3+2]-cycloaddition reaction of azomethine ylides, derived from isatin/N-benzylisatin and sarcosine, with various porphyrin derivatives as dipolarophiles.
引用
收藏
页码:2329 / 2335
页数:7
相关论文
共 50 条
  • [21] 3+2 Cycloadditions on azomethine ylides
    Backous, Jeffrey P.
    Jasperse, Craig P.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 692 - 692
  • [22] Enantioselective ag(i)-catalyzed [3+2] cycloaddition of azomethine ylides.
    Zhang, XM
    Raghunath, M
    Longmire, J
    Wang, B
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U208 - U208
  • [23] CuI-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Cyclobutenones
    Corpas, Javier
    Ponce, Alberto
    Adrio, Javier
    Carretero, Juan C.
    [J]. ORGANIC LETTERS, 2018, 20 (11) : 3179 - 3182
  • [24] A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES
    BERGSTRASSER, U
    HOFFMANN, A
    REGITZ, M
    [J]. TETRAHEDRON LETTERS, 1992, 33 (08) : 1049 - 1052
  • [25] Catalytic Enantioselective [3+2] Cycloaddition of N-Metalated Azomethine Ylides
    Kumar, Sundaravel Vivek
    Guiry, Patrick J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)
  • [26] Bifunctional AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Zeng, W
    Zhou, YG
    [J]. ORGANIC LETTERS, 2005, 7 (22) : 5055 - 5058
  • [27] Synthesis of polysubstituted fused pyrrolidines via [2+2]/[2+3] cycloaddition of azomethine ylides
    Ou, Chunyan
    Wang, Jian
    Yin, Pingping
    Chen, Bin
    Hu, Ping
    Wang, Bi-Qin
    Cao, Peng
    Xu, Minghui
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (15): : 4149 - 4155
  • [28] 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
  • [29] [3+2] cycloaddition of nonstabilized azomethine ylides. 7. Stereoselective synthesis of epibatidine and analogues
    Pandey, G
    Bagul, TD
    Sahoo, AK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 760 - 768
  • [30] [3+2] Cycloaddition of metal-containing azomethine ylides for highly efficient synthesis of mitosene skeleton
    Takaya, Jun
    Miyashita, Yuichi
    Kusama, Hiroyuki
    Iwasawa, Nobuharu
    [J]. TETRAHEDRON, 2011, 67 (24) : 4455 - 4466