One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes

被引:8
作者
Li, Yunlan [1 ]
Zhang, Qiurui [1 ]
Xu, Xuefeng [1 ]
Zhang, Xu [1 ]
Yang, Yurong [2 ,3 ,4 ]
Yi, Wei [2 ,3 ,4 ]
机构
[1] Nanyang Normal Univ, Sch Chem & Pharmacony Engn, Nanyang 473061, Peoples R China
[2] Guangzhou Med Univ, Sch Pharmaceut Sci, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China
[3] Guangzhou Med Univ, Sch Pharmaceut Sci, State Key Lab Resp Dis, Guangzhou 511436, Guangdong, Peoples R China
[4] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
AgOTf catalyst; Amines; Alkyne esters; Terminal alkynes; 2,4-Disubstituted quinolines; C-H ACTIVATION; REGIOSELECTIVE SYNTHESIS; OXIDATIVE ANNULATION; TANDEM SYNTHESIS; DERIVATIVES; FUNCTIONALIZATION; ACCESS; ALDEHYDES; ANILINES; DIARYLIODONIUMS;
D O I
10.1016/j.tetlet.2019.03.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facile formation of the enamine species with the feature of good to excellent yields, exclusive regioselectivity, and excellent substrate/functional group tolerance. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:965 / 970
页数:6
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共 75 条
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] New processes for the synthesis of biologically relevant heterocycles
    Banwell, Martin G.
    [J]. PURE AND APPLIED CHEMISTRY, 2008, 80 (04) : 669 - 679
  • [3] Recognition of Adenosine Monophosphate and H2PO4- using Zinc Ensemble of New Hexaphenylbenzene Derivative: Potential Bioprobe and Multichannel Keypad System
    Bhalla, Vandana
    Vij, Varun
    Kumar, Manoj
    Sharma, Parduman Raj
    Kaur, Tandeep
    [J]. ORGANIC LETTERS, 2012, 14 (04) : 1012 - 1015
  • [4] Iron(III)-Catalyzed and Air-Mediated Tandem Reaction of Aldehydes, Alkynes and Amines: An Efficient Approach to Substituted Quinolines
    Cao, Ke
    Zhang, Fu-Min
    Tu, Yong-Qiang
    Zhuo, Xiao-Tao
    Fan, Chun-An
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) : 6332 - 6334
  • [5] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds
    Chen, Feng
    Wang, Teng
    Jiao, Ning
    [J]. CHEMICAL REVIEWS, 2014, 114 (17) : 8613 - 8661
  • [6] Synthesis of Quinoline Derivatives via Cu-Catalyzed Cascade Annulation of Heterocumulenes, Alkynes, and Diaryliodonium Salts
    Chi, Yen
    Yan, Haihan
    Zhang, Wen-Xiong
    Xi, Zhenfeng
    [J]. ORGANIC LETTERS, 2017, 19 (10) : 2694 - 2697
  • [7] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
  • [8] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions
    Colby, Denise A.
    Tsai, Andy S.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 814 - 825
  • [9] Copper(II) catalyzed domino synthesis of quinoline derivatives from arylamines and alkynes
    Dai, Huimin
    Li, Chun-Xiao
    Yu, Chao
    Wang, Zihao
    Yan, Hong
    Lu, Changsheng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10): : 2008 - 2011
  • [10] Transition-Metal-Catalyzed C-H Alkylation Using Alkenes
    Dong, Zhe
    Ren, Zhi
    Thompson, Samuel J.
    Xu, Yan
    Dong, Guangbin
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9333 - 9403