Copper-catalyzed C-H alkylation of 8-aminoquinolines via 8-amide chelation assistance

被引:31
|
作者
Xia, Xiao-Feng [1 ]
Zhu, Su-Li [1 ]
Gu, Zhen [1 ]
Wang, Haijun [1 ]
机构
[1] Jiangnan Univ, Sch Chem & Mat Engn, Minist Educ, Key Lab Food Colloids & Biotechnol, Wuxi 214122, Jiangsu, Peoples R China
来源
RSC ADVANCES | 2015年 / 5卷 / 37期
基金
美国国家科学基金会;
关键词
QUINOLINE N-OXIDES; ALIPHATIC CARBOXYLIC-ACIDS; ALPHA-AMINO-ACIDS; MILD CONDITIONS; ARYL HALIDES; DIRECTING GROUP; C-8; POSITION; ARYLATION; AGENTS; ANTIMALARIALS;
D O I
10.1039/c4ra16896h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed 8-amide chelation- assisted C-H alkylation of 8-aminoquinolines is described. The secondary and tertiary alkyl carboxylic acids can be used as alkylating agents. This reaction allows for the highly regioselective preparation of C2-adamantyl 8-aminoquinoline scaffolds by the decarboxylative alkylation catalytic system.
引用
收藏
页码:28892 / 28895
页数:4
相关论文
共 50 条
  • [41] Copper-catalyzed electrochemical C-H fluorination
    Hintz, Heather
    Bower, Jamey
    Tang, Jinghua
    LaLama, Matthew
    Sevov, Christo
    Zhang, Shiyu
    CHEM CATALYSIS, 2023, 3 (01):
  • [42] Copper-Catalyzed Electrophilic Amination of Heteroarenes via C-H Alumination
    Yoon, Hongju
    Lee, Yunmi
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10244 - 10251
  • [43] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [44] Copper-Catalyzed C-H Alkoxylation of Azoles
    Takemura, Noriaki
    Kuninobu, Yoichiro
    Kanai, Motomu
    ORGANIC LETTERS, 2013, 15 (04) : 844 - 847
  • [45] Copper-catalyzed allylic C-H phosphonation
    Yang, Bin
    Zhang, Hong-Yu
    Yang, Shang-Dong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3561 - 3565
  • [46] Copper-Mediated and Catalyzed C-H Bond Amination via Chelation Assistance: Scope, Mechanism and Synthetic Applications
    Ma, Jiao-Li
    Zhou, Xu-Ming
    Guo, Peng-Hu
    Cheng, Hui-Cheng
    Ji, Hong-bing
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (10) : 1204 - 1223
  • [47] Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles
    Mishra, Subhajit
    Mondal, Pallab
    Ghosh, Monoranjan
    Mondal, Susmita
    Hajra, Alakananda
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) : 1432 - 1436
  • [48] Copper-Catalyzed ortho-Thiomethylation of Benzamides via 8-Aminoquinoline-Assisted C-H Activation with Dimethyl Sulfoxide
    Cui, Xinfeng
    Liu, Xingxing
    Wang, Xiajun
    Tian, Wanfa
    Wei, Daidong
    Huang, Guosheng
    CHEMISTRYSELECT, 2017, 2 (27): : 8607 - 8611
  • [49] Nano-CuO catalyzed one-pot C-H azidation/azide-alkyne cycloaddition for triazole-substituted 8-aminoquinolines
    Sheng, Li
    Shen, Dadong
    Zhu, Jinlin
    Wu, Guofeng
    Fan, Gang
    Wu, Xufeng
    Du, Kui
    TETRAHEDRON, 2021, 85
  • [50] Catalyst controlled remote C-H activation of 8-aminoquinolines with NFSI for C-N versus C-F coupling
    Zheng, Kai
    Zhou, Enmu
    Zhang, Letian
    Zhang, Lixi
    Yu, Wenbo
    Xu, Hao
    Shen, Chao
    CATALYSIS COMMUNICATIONS, 2021, 158