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

被引:79
|
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
  • [1] Gold catalyzed enantioselective intermolecular [3+2] dipolar cycloaddition of N-allenyl amides with nitrones
    Li, Guo-Hua
    Zhou, Wen
    Li, Xiao-Xiao
    Bi, Qing-Wei
    Wang, Zhen
    Zhao, Zhi-Gang
    Hu, Wen-Xiang
    Chen, Zili
    CHEMICAL COMMUNICATIONS, 2013, 49 (42) : 4770 - 4772
  • [2] Alkaloid-Catalyzed Enantioselective [3+2] Cycloaddition of Ketenes and Azomethine Imines
    Mondal, Mukulesh
    Wheeler, Kraig A.
    Kerrigan, Nessan J.
    ORGANIC LETTERS, 2016, 18 (16) : 4108 - 4111
  • [3] Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines
    Mao, Biming
    Zhang, Junya
    Xu, Yi
    Yan, Zhengyang
    Wang, Wei
    Wu, Yongjun
    Sun, Changqing
    Zheng, Bing
    Guo, Hongchao
    CHEMICAL COMMUNICATIONS, 2019, 55 (85) : 12841 - 12844
  • [4] Chiral-Boron-Complex-Catalyzed Asymmetric [3+2] Cycloaddition of 2′-Hydroxychalcones with N,N′-Cyclic Azomethine Imines
    Chai, Guo-Li
    Yao, En-Ze
    Liu, Rui-Hao
    Chang, Junbiao
    ORGANIC LETTERS, 2022, 24 (35) : 6449 - 6454
  • [5] Thermal [3+2] Cycloaddition of Aromatic Azomethine Imines with Allenoates
    Zhang, Lei
    Jing, Chengfeng
    Liu, Honglei
    Wang, Bo
    Li, Zhen
    Jiang, Hui
    Yu, Hao
    Guo, Hongchao
    SYNTHESIS-STUTTGART, 2013, 45 (01): : 53 - 64
  • [6] Catalytic asymmetric [3+2] cycloaddition of azomethine imines with ketenes
    Mondal, Mukulesh
    Kerrigan, Nessan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [7] Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates
    Zhang, Zhibin
    Bender, Christopher F.
    Widenhoefer, Ross A.
    ORGANIC LETTERS, 2007, 9 (15) : 2887 - 2889
  • [8] Asymmetric [3+2] Cycloaddition of Methyleneindolinones with N,N′-Cyclic Azomethine Imines Catalyzed by a N,N′-Dioxide Mg(OTf)2 Complex
    Yin, Chengkai
    Lin, Lili
    Zhang, Dong
    Feng, Juhua
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9691 - 9699
  • [9] Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′-Cyclic azomethine imines
    Jovanovic, Jovana P.
    Novakovic, Sladjana B.
    Bogdanovic, Goran A.
    Minic, Aleksandra
    Pejovic, Anka
    Katanic, Jelena
    Mihailovic, Vladimir
    Nastasijevic, Branislav
    Stevanovic, Dragana
    Damljanovic, Ivan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 860 : 85 - 97
  • [10] Acid-Catalyzed [3+2] Cycloaddition of Enones with Azomethine Imines for Easy Access to Tetrahydropyrazolopyrazolones
    Jovanovic, Jovana P.
    Bogdanovic, Goran A.
    Damljanovic, Ivan
    SYNLETT, 2017, 28 (06) : 664 - 668