Synthesis of 2-Trifluoromethyl Quinoline by the Reaction of Fluorinated Imine with Alkyne Catalyzed by Indium(III) Triflate

被引：22
作者：
Xie, Haibo [1 ]
Zhu, Jiangtao [1 ]
Chen, Zixian [1 ,2 ]
Li, Shan [1 ]
Wu, Yongming [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Huazhong Univ Sci & Technol, Dept Chem, Wuhan 430074, Hubei, Peoples R China
来源：
SYNLETT | 2010年 / 17期
基金：
美国国家科学基金会;
关键词：
alkynes; quinolines; indium; Diels-Alder reaction; imines; ONE-POT SYNTHESIS; SUBSTITUTED QUINOLINES; ARYLIMIDOYL RADICALS; AROMATIC ANNELATION; EFFICIENT SYNTHESIS; BRONSTED ACID; DERIVATIVES; CYCLIZATION; CHLORIDES; AMINES;
D O I：
10.1055/s-0030-1258770
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Preparation of 2-trifluoromethyl-4-aryl quinolines from a variety of readily available alkynes and N-aryl trifluoroethylimine has been achieved via indium(III) triflate catalyzed Diels-Alder reactions.
引用
收藏
页码：2659 / 2663
页数：5
相关论文
共 32 条
  • [1] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines
    Amii, H
    Kishikawa, Y
    Uneyama, K
    [J]. ORGANIC LETTERS, 2001, 3 (08) : 1109 - 1112
  • [2] Baraznenok IL, 1999, EUR J ORG CHEM, V1999, P937
  • [3] A fluorobenzene adduct of Ti(IV), and catalytic carboamination to prepare α,β-unsaturated imines and triaryl-substituted quinolines
    Basuli, F
    Aneetha, H
    Huffman, JC
    Mindiola, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 17992 - 17993
  • [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] Palladium catalyzed synthesis of 2-trifluoromethylquinolines through a domino Sonogashira-alkyne carbocyclization process
    Chen, Zixian
    Zhu, Jiangtao
    Xie, Haibo
    Li, Shan
    Wu, Yongming
    Gong, Yuefa
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (12) : 2145 - 2147
  • [6] Combes A., 1888, B CHIM SOC FRANCE, V49, P89
  • [7] Synthesis of tetrahydroquinoline derivatives from α-CF3-N-arylaldimine and vinyl ethers
    Crousse, B
    Bégué, JP
    Bonnet-Delpon, D
    [J]. TETRAHEDRON LETTERS, 1998, 39 (32) : 5765 - 5768
  • [8] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine
    Crousse, B
    Bégué, JP
    Bonnet-Delpon, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 5009 - 5013
  • [9] Synthesis of 2-substituted trifluoromethylquinolines for the evaluation of leishmanicidal activity
    Dade, J
    Provot, O
    Moskowitz, H
    Mayrargue, J
    Prina, E
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (04) : 480 - 483
  • [10] Dyke H.J., 2000, [No title captured], Patent No. 2000026208
1234