Facile synthesis of CF3-substituted dienamides via one-pot tandem reactions

被引:6
作者
Yuan, Zhe-Zhe [1 ]
Kong, Xiang-Wen [1 ]
Liu, Li-Hua [1 ]
Zhu, Hui-Xia [1 ]
Xiao, Hua [1 ,2 ]
机构
[1] Hefei Univ Technol, Dept Pharmaceut Engn, Hefei 230009, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Dienamides; Aminolysis; Butenolide; Phosphine catalysis; One-pot; TRIFLUOROMETHYL KETONES; DIRECT AMIDATION; PHOSPHINE; CATALYST; CYCLOADDITION; DERIVATIVES; CYCLIZATIONS; CARBONATES; ESTERS; DBU;
D O I
10.1016/j.cclet.2017.02.017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot reaction sequence of sequential phosphine-promoted tandem annulations of aryl trifluoromethyl ketones and MBH (Morita-Baylis-Hillman) carbonates and DBU-mediated aminolysis was developed. This method provides a step-economical approach to trifluoromethylated dienamides with diverse structural complexity from readily available starting materials in moderate yields. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1469 / 1472
页数:4
相关论文
共 32 条
  • [1] Catalytic amidation of unactivated ester derivatives mediated by trifluoroethanol
    Caldwell, Nicola
    Jamieson, Craig
    Simpson, Iain
    Watson, Allan J. B.
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (46) : 9495 - 9498
  • [2] Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates
    D'Souza, Brendan R.
    Louie, Janis
    [J]. ORGANIC LETTERS, 2009, 11 (18) : 4168 - 4171
  • [3] Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition-Claisen Rearrangement-Dehydrobromination Cascade Reaction of Ynsulfonamides
    Ding, Runbo
    Li, Yun
    Tao, Cheng
    Cheng, Bin
    Zhai, Hongbin
    [J]. ORGANIC LETTERS, 2015, 17 (16) : 3994 - 3997
  • [4] Phosphine-promoted [3+2] cycloaddition between nonsubstituted MBH carbonates and trifluoromethyl ketones
    Duan, Hong-Yu
    Ma, Juan
    Yuan, Zhe-Zhe
    Yao, Ri-Sheng
    Tao, Wei
    Xu, Fang
    Xiao, Hua
    Zhao, Gang
    [J]. CHINESE CHEMICAL LETTERS, 2015, 26 (06) : 646 - 648
  • [5] El Ali B, 2012, TETRAHEDRON LETT, V53, P6535, DOI [10.1016/j.tetlet.2012.09.084, DOI 10.1016/J.TETLET.2012.09.084]
  • [6] Enantioselective Synthesis of Isoquinolines: Merging Chiral-Phosphine and Gold Catalysis
    Gao, Yu-Ning
    Shi, Feng-Chen
    Xu, Qin
    Shi, Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6803 - 6807
  • [7] ASPECTS OF THE METABOLISM OF VALPROIC ACID
    GRANNEMAN, GR
    WANG, SI
    MACHINIST, JM
    KESTERSON, JW
    [J]. XENOBIOTICA, 1984, 14 (05) : 375 - 387
  • [8] Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates
    Han, Xiaoyu
    Chan, Wai-Lun
    Yao, Weijun
    Wang, Yongjiang
    Lu, Yixin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (22) : 6492 - 6496
  • [9] Phosphine-Catalyzed [3+3]-Domino Cycloaddition of Ynones and Azomethine Imines To Construct Functionalized Hydropyridazine Derivatives
    Liang, Ling
    Huang, You
    [J]. ORGANIC LETTERS, 2016, 18 (11) : 2604 - 2607
  • [10] Reagent-Controlled Tandem Reactions of Vinyl Epoxides: Access to Functionalized γ-Butenolides
    Ma, Juan
    Yuan, Zhe-zhe
    Kong, Xiang-wen
    Wang, Huai
    Li, Yi-ming
    Xiao, Hua
    Zhao, Gang
    [J]. ORGANIC LETTERS, 2016, 18 (06) : 1450 - 1453