Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins

被引：51
|
作者：
Shen, Yang [1 ]
Cui, Sunliang [1 ]
Wang, Jing [1 ]
Chen, Xiaopeng [1 ]
Lu, Ping [1 ]
Wang, Yanguang [1 ,2 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 07期
基金：
中国国家自然科学基金;
关键词：
cascade reactions; copper; coumarins; ketenimines; multicomponent reactions; ONE-POT SYNTHESIS; FLUORESCENT CA2+ INDICATORS; MULTICOMPONENT REACTION; SULFONYL AZIDES; FACILE ACCESS; ENANTIOENRICHED PIPERIDINES; EFFICIENT SYNTHESIS; CASCADE REACTIONS; AMIDE SYNTHESIS; WATER;
D O I：
10.1002/adsc.200900890
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient synthesis of N-sulfonyl-substituted 2-imino-3,4-dihydrocoumarins and 2-iminocoumarins via a copper-catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and beta-(ortho-hydroxypheny1)-alpha,beta-unsaturated ketones or ortho-hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.
引用
收藏
页码：1139 / 1144
页数：6
相关论文
共 50 条
  • [41] A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions
    Pasunooti, Kalyan Kumar
    Chai, Hua
    Jensen, Chantel Nixon
    Gorityala, Bala Kishan
    Wang, Siming
    Liu, Xue-Wei
    [J]. TETRAHEDRON LETTERS, 2011, 52 (01) : 80 - 84
  • [42] Copper-catalyzed three-component synthesis of pyrrole-substituted 1,2-dihydroisoquinolines
    Floyd, Matthew D.
    Ryan, Lianne Y.
    Hendsey, Jessica L.
    Nicholson, Joshua M.
    Palaia, Andrew T.
    Isaacs, Andre K.
    [J]. SYNTHETIC COMMUNICATIONS, 2022, 52 (05) : 755 - 763
  • [43] Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes
    Kennedy-Ellis, Jonathan J.
    Boldt, Erik D.
    Chemler, Sherry R.
    [J]. ORGANIC LETTERS, 2020, 22 (21) : 8365 - 8369
  • [44] Copper-Catalyzed Three-Component Domino Cyclization for the Synthesis of 4-Aryl-5-(arythio)-2-(trifluoromethyl)oxazoles
    Xiao, Fuhong
    Yuan, Shanshan
    Huang, Huawen
    Zhang, Feng
    Deng, Guo-Jun
    [J]. ORGANIC LETTERS, 2019, 21 (21) : 8533 - 8536
  • [45] Three-component one-pot synthesis of&IT N&IT-arylsulfonyl-2-iminocoumarins
    Mandal, Prashant S.
    Kumar, A. Vijay
    [J]. TETRAHEDRON, 2018, 74 (15) : 1900 - 1907
  • [46] Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction
    Cui, Sun-Liang
    Lin, Xu-Feng
    Wang, Yan-Guang
    [J]. ORGANIC LETTERS, 2006, 8 (20) : 4517 - 4520
  • [47] One-pot copper-catalyzed three-component reaction: a modular approach to functionalized 2-quinolones
    Kim, Ah Reum
    Lim, Hee Nam
    [J]. RSC ADVANCES, 2020, 10 (13) : 7855 - 7866
  • [48] Copper-Catalyzed Three-Component Difunctionalization of Aromatic Alkenes with 2-Amino-1,4-naphthoquinones and α-Bromocarboxylates
    Yu Shangguan
    Yang, Fazhou
    Deng, Hao
    Liu, Hao
    Liu, Ziyan
    Zhuang, Wanyue
    Qiao, Chenxi
    Wang, Aizheng
    Xiao, Yumei
    Zhang, Cheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 10649 - 10657
  • [49] Copper-catalyzed three-component formal [3+1+2] annulations for the synthesis of 2-aminopyrimidines from O-acyl ketoximes
    Xu, Zhenhua
    Chen, Hongbiao
    Deng, Guo-Jun
    Huang, Huawen
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (40) : 8706 - 8710
  • [50] Copper-Catalyzed Three-Component Reactions of 2-Iodo-2,2-difluoroacetophenones, Alkynes, and Trimethylsilyl Cyanide
    Wu, Pingjie
    Zheng, Cheng
    Wang, Xia
    Wu, Jingjing
    Wu, Fanhong
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (09) : 1420 - 1423
12345