Gold catalyzed [3+2] cycloaddition of N-allenyl amides with azomethine imines

被引:80
作者
Zhou, Wen [1 ]
Li, Xiao-Xiao [1 ]
Li, Guo-Hua [1 ]
Wu, Yun [2 ]
Chen, Zili [1 ]
机构
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
关键词
ASYMMETRIC-SYNTHESIS; ENOL ETHER; HYDROAMINATION; ALLENAMIDES; ACCESS;
D O I
10.1039/c3cc41258j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gold(I) catalyzed [3+2] cycloaddition of azomethine imines with N-allenyl amides was developed to provide two types of pyrazolyl based bicyclic heterocycles. Both pyrazolidin-3-one derived and dihydroisoquinoline derived azomethine imines reacted smoothly with N-allenyl amides to give 6-methylene bipyrazolidin-1-ones and 1-methylene hexahydropyrazolo[5,1-a] isoquinolines in moderate to good yields.
引用
收藏
页码:3552 / 3554
页数:3
相关论文
共 50 条
  • [31] An expedient synthesis of ferrocene grafted spirooxindolopyrrolizidines via [3+2]-cycloaddition of azomethine ylides
    Babu, A. R. Suresh
    Raghunathan, R.
    Baskaran, Sundari
    TETRAHEDRON, 2009, 65 (11) : 2239 - 2243
  • [32] Chiral Silver Amides as Effective Catalysts for Enantioselective [3+2] Cycloaddition Reactions
    Yamashita, Yasuhiro
    Imaizumi, Takaki
    Guo, Xun-Xiang
    Kobayashi, Shu
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (09) : 2550 - 2559
  • [33] Phosphine-Catalyzed Highly Enantioselective [3+3] Cycloaddition of Morita-Baylis-Hillman Carbonates with C,N-Cyclic Azomethine Imines
    Zhang, Lei
    Liu, Honglei
    Qiao, Guanyu
    Hou, Zhanfeng
    Liu, Yang
    Xiao, Yumei
    Guo, Hongchao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (13) : 4316 - 4319
  • [34] Lewis Acid Catalyzed Intramolecular [4+2] and [3+2] Cross-Cycloaddition of Alkynylcyclopropane Ketones with Carbonyl Compounds and Imines
    Bai, Yu
    Tao, Weijie
    Ren, Jun
    Wang, Zhongwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) : 4112 - 4116
  • [35] Diastereo- and Enantioselective Silver-Catalyzed [3+3] Cycloaddition and Kinetic Resolution of Azomethine Imines with Activated Isocyanides
    Tao, Ling-Fei
    Zhang, Sen
    Huang, Fen
    Wang, Wen-Tao
    Luo, Zhang-Hong
    Qian, Linghui
    Liao, Jia-Yu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (23)
  • [36] A simple one-pot preparation of N-allenyl amides, ureas, carbamates and sulfonamides using a DMSO/tBuOK protocol
    Bousfield, Thomas W.
    Kimber, Marc C.
    TETRAHEDRON LETTERS, 2015, 56 (02) : 350 - 352
  • [37] Gold-catalyzed intermolecular formal (3+2) cycloaddition of stabilized vinyldiazo derivatives and electronically unbiased allenes
    Lopez, Enol
    Lonzi, Giacomo
    Gonzalez, Javier
    Lopez, Luis A.
    CHEMICAL COMMUNICATIONS, 2016, 52 (60) : 9398 - 9401
  • [38] Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Han, Fu-Zhong
    Yu, Sai-Bo
    Zhang, Cheng
    Hu, Xiang -Ping
    TETRAHEDRON, 2016, 72 (21) : 2616 - 2622
  • [39] Enantioselective [3+2] cycloaddition of azomethine ylides and aldehydes via Ni/bis(oxazoline)-catalyzed ring opening of N-tosylaziridines through a chirality transfer approach
    Wu, Xingxing
    Zhou, Wei
    Wu, Hai-Hong
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2017, 53 (41) : 5661 - 5664
  • [40] Sc(OTf)3-catalyzed [3+2]-cycloaddition of nitrones with ynones
    He, Chun-Ting
    Han, Xiao-Li
    Zhang, Yan-Xue
    Du, Zhen-Ting
    Si, Chang-Mei
    Wei, Bang-Guo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (02) : 457 - 466