Ytterbium-catalyzed formal [4+2] cycloaddition: Synthesis of chalcogen-quinolines 3-unsubstituted

被引:3
|
作者
de Oliveira, Isadora M. [1 ]
Darbem, Mariana P. [2 ]
Esteves, C. Henrique A. [2 ]
Pimenta, Daniel C. [3 ]
Zukerman-Schpector, Julio [4 ]
Stefani, Helio A. [2 ]
Manarin, Flavia [5 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP, Brazil
[2] Univ Sao Paulo, Fac Ciencias Farmacaut, Dept Farm, Sao Paulo, Brazil
[3] Inst Butantan, Sao Paulo, SP, Brazil
[4] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP, Brazil
[5] Univ Estadual Oeste Parana, CECE, Toledo, PR, Brazil
基金
巴西圣保罗研究基金会;
关键词
Quinolines; Ytterbium; Poly-substituted quinolones; Selenium; Internal alkynes; POLYSUBSTITUTED QUINOLINES; SUBSTITUTED QUINOLINES; TANDEM SYNTHESIS; 5+1 ANNULATION; DERIVATIVES; SELENIUM; ALKYNES; CHEMISTRY; EFFICIENT;
D O I
10.1016/j.tetlet.2018.09.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective ytterbium-catalyzed annulation reaction between ethylglyoxalate, anilines and silylalkynes bearing selenyl- and telluryl-moieties for the formation of poly-substituted quinolones is described. A series of examples formed under mild conditions are presented, including a scaled-up reaction and a study on catalyst recyclability. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3907 / 3911
页数:5
相关论文
共 50 条
  • [31] Palladium-catalyzed intermolecular [4+2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides
    Yan, Fachao
    Liang, Hanbing
    Ai, Bing
    Liang, Wenjing
    Jiao, Luyang
    Yao, Shuzhi
    Zhao, Pingping
    Liu, Qing
    Dong, Yunhui
    Liu, Hui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (10) : 2651 - 2656
  • [32] Stereoselective synthesis of tetrahydropyrans via formal [4+2]-cycloaddition: A comparison of allylsilane and crotylsilane
    Angle, SR
    Belanger, DS
    El-Said, NA
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22): : 7699 - 7705
  • [33] New Ytterbium Complex-catalyzed Multicomponent Reactions for Synthesis of Dihydropyrimidines: [4+2] Cycloaddition vs. Biginelli Type Reaction
    Zhu, Jie
    Zhang, Mingjie
    Liu, Bo
    Li, Xiaojuan
    CHEMISTRY LETTERS, 2009, 38 (01) : 56 - 57
  • [34] Copper Catalyzed Inverse Electron Demand [4+2] Cycloaddition for the Synthesis of Oxazines
    Yang, Weiguang
    Zhou, Zitong
    Zhao, Yu
    Luo, Danyang
    Luo, Xiai
    Luo, Hui
    Cui, Liao
    Li, Li
    CATALYSTS, 2022, 12 (05)
  • [35] Gold(I)-Catalyzed Generation of the Two Components of a Formal [4+2] Cycloaddition Reaction for the Synthesis of Tetracyclic Pyrano[2,3,4-de]chromenes
    Arto, Tamara
    Fananas, Francisco J.
    Rodriguez, Felix
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7218 - 7221
  • [36] Gold-Catalyzed Formal [4+2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[g]quinolines
    Chen, Xiaoyu
    Merrett, James Theodore
    Chan, Philip Wai Hong
    ORGANIC LETTERS, 2018, 20 (06) : 1542 - 1545
  • [37] ORGN 635-Synthesis of polycyclic cycloheptadienes by the nickel-catalyzed [3+2+2] cycloaddition and sequential [4+2] cycloaddition
    Komagawa, Shinsuke
    Takeuchi, Kouhei
    Sotome, Ikuo
    Yamasaki, Ryu
    Saito, Shinichi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [38] Iridium-catalyzed enantioselective formal [4+2] cycloaddition of biphenylene and alkynes for the construction of axial chirality
    Shibata, Takanori
    Nishizawa, Go
    Endo, Kohei
    SYNLETT, 2008, (05) : 765 - 768
  • [39] Access to 1,2-Dihydroisoquinolines through Gold-Catalyzed Formal [4+2] Cycloaddition
    Xin, Zhuo
    Kramer, Soren
    Overgaard, Jacob
    Skrydstrup, Troels
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) : 7926 - 7930
  • [40] Yb(OTf)3-catalyzed [4+2] cycloaddition of allenyltrimethylsilylthioketenes with arylaldimines
    Aoyagi, Shigenobu
    Ohata, Satoru
    Shimada, Kazuaki
    Takikawa, Yuji
    SYNLETT, 2007, (04) : 615 - 618