Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines

被引：6
|
作者：
Hao, Wenyan [1 ]
Wang, Yuyun [1 ]
Yang, Guomin [1 ]
Liu, Yunyun [1 ]
机构：
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 37卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Nickel-catalyze; C-H halogenation; N-bromo-succinimide; 8-aminoquinolines; dihalogenated quinoline; C(SP(3))-H BONDS; ARYLATION; COPPER; DISCOVERY; SCAFFOLD; HALIDES; ISOINDOLINONES; CYCLOADDITION; HETEROCYCLES; CHLORINATION;
D O I：
10.6023/cjoc201704049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient nickel-catalyzed oxidative halogenation (Cl, Br) of C(5) and C(7) C-H bond of 8-aminoquinoline amides has been developed. This method employed low-cost and easy availability nickel as catalyst and oxygen as oxidant. The reactions have good functional groups compatibility, giving highly selective C(5) and C(7) di-halogenated products in good to excellent yields.
引用
收藏
页码：2678 / 2684
页数：7
相关论文
共 52 条
  • [1] Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy
    Abouelhassan, Yasmeen
    Garrison, Aaron T.
    Burch, Gena M.
    Wong, Wilson
    Norwood, Verrill M.
    Huigens, Robert W., III
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (21) : 5076 - 5080
  • [2] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines
    Berman, Ashley M.
    Lewis, Jared C.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 14926 - +
  • [3] Substituted oxines inhibit endothelial cell proliferation and angiogenesis
    Bhat, Shridhar
    Shim, Joong Sup
    Zhang, Feiran
    Chong, Curtis Robert
    Liu, Jun O.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) : 2979 - 2992
  • [4] CATECHOL O-METHYLTRANSFERASE .2. IN-VITRO INHIBITION BY SUBSTITUTED 8-HYDROXYQUINOLINES
    BORCHARDT, RT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (04) : 382 - 387
  • [5] Multiple regioselective functionalizations of quinolines via magnesiations
    Boudet, Nadege
    Lachs, Jennifer R.
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2007, 9 (26) : 5525 - 5528
  • [6] Transition-Metal-Free BF3-Mediated Regioselective Direct Alkylation and Arylation of Functionalized Pyridines Using Grignard or Organozinc Reagents
    Chen, Quan
    du Jourdin, Xavier Mollat
    Knochel, Paul
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (13) : 4958 - 4961
  • [7] Synthesis of isoindolinones via carbonylative cyclisation of 2-(2-bromophenyl)-2-oxazolines by a bimetallic palladium-nickel catalyst system
    Cho, CS
    Lee, JW
    Lee, DY
    Shim, SC
    Kim, TJ
    [J]. CHEMICAL COMMUNICATIONS, 1996, (18) : 2115 - 2116
  • [8] Efficient Oxidative Chlorination of Aromatics on Saturated Sodium Chloride Solution
    Gu, Liuqun
    Lu, Ting
    Zhang, Mingyun
    Tou, Lijuan
    Zhang, Yugen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1077 - 1082
  • [9] Copper and palladium mediated C-H chlorination on 8-acylaminoquinoline scaffolds
    Guo, Haili
    Chen, Miaomiao
    Jiang, Peng
    Chen, Jian
    Pan, Lingxia
    Wang, Min
    Xie, Chunsong
    Zhang, Yuhong
    [J]. TETRAHEDRON, 2015, 71 (01) : 70 - 76
  • [10] Nickel-Catalyzed Oxidative C-H/N-H Isocyanide Insertion: An Efficient Synthesis of Iminoisoindolinone Derivatives
    Hao, Wenyan
    Tian, Jun
    Li, Wu
    Shi, Renyi
    Huang, Zhiliang
    Lei, Aiwen
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (11) : 1664 - 1667
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