Synthesis of 3-acylquinolines through Cu-catalyzed double C(sp3)-H bond functionalization of saturated ketones

被引:39
|
作者
Wang, Ze [1 ]
Chen, Guang [1 ]
Zhang, Xinying [1 ]
Fan, Xuesen [1 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Key Lab Green Chem Media & React,Minist Educ, Xinxiang 453007, Henan, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 04期
基金
中国国家自然科学基金;
关键词
AEROBIC DEHYDROGENATION; SUBSTITUTED QUINOLINES; DERIVATIVES; INHIBITORS; ANNULATION; ACCESS; CYCLOHEXANONE; HETEROCYCLES; CYCLIZATION; PROTEIN;
D O I
10.1039/c6qo00817h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel synthesis of 3-acylquinolines from Cu-catalyzed one-pot reactions of 2-aminoaryl aldehydes/ketones with inactivated ketones is presented. Mechanistically, the formation of the title compounds involves a cascade procedure including C(sp3)-H bond amination, enaminone formation, and enamine-carbonyl condensation. To our knowledge, this should be the first example in which 3-acylquinolines are prepared through Cu-catalyzed double C(sp3)-H bond functionalization of saturated ketones.
引用
收藏
页码:612 / 616
页数:5
相关论文
共 50 条
  • [1] Cu-Catalyzed [3+3] Annulation for the Synthesis of Pyrimidines via β-C(sp3)-H Functionalization of Saturated Ketones
    Zhan, Jun-Long
    Wu, Meng-Wei
    Chen, Fei
    Han, Bing
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 11994 - 12000
  • [2] Cu-Catalyzed α-Alkylation of Glycine Derivatives for C(sp3)-H/C(sp3)-H Bond Selective Functionalization
    Xiang, Huan
    Ye, Yang
    ACS CATALYSIS, 2023, 14 (01) : 522 - 532
  • [3] Cu-Catalyzed Double C(sp3)-H Functionalization of Ethylarenes to Form Arylethanolamines
    Oku, Naoki
    Miura, Tomoya
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7592 - 7596
  • [4] Cu-Catalyzed Polychloromethylamination of Styrenes through C(sp3)-H Bond Cleavage
    Zhu, Fengxiang
    Xue, Jianxin
    Yin, Pengpeng
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (17)
  • [5] Cu-Catalyzed aerobic oxidative cleavage of C(sp3)-C(sp3) bond: Synthesis of α-ketoamides
    Zhang, Jingming
    Liu, Chengkou
    Yang, Man
    Fang, Zheng
    Guo, Kai
    TETRAHEDRON LETTERS, 2020, 61 (47)
  • [6] Cu-catalyzed selective cascade sp3 C-H bond oxidative functionalization towards isoxazoline derivatives
    Wang, Gang-Wei
    Cheng, Ming-Xing
    Ma, Ran-Song
    Yang, Shang-Dong
    CHEMICAL COMMUNICATIONS, 2015, 51 (29) : 6308 - 6311
  • [7] Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation
    Takale, Balaram S.
    Thakore, Ruchita R.
    Etemadi-Davan, Elham
    Lipshutz, Bruce H.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 691 - 737
  • [8] Cu-Catalyzed Regioselective Heteroarylation of C(sp3)-H Bond Induce by Sulfonyl Group
    Liu, Huiying
    Wu, Zhongtian
    Li, Haotian
    Wu, Xinxin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2025, 45 (01) : 297 - 306
  • [9] Gold-catalyzed C(sp3)-H bond functionalization
    Xie, Jin
    Pan, Changduo
    Abdukader, Ablimit
    Zhu, Chengjian
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) : 5245 - 5256
  • [10] Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts through C-C Bond Formation on Inert C(sp3)-H Bond
    Peng, Jing
    Chen, Chao
    Chen, Junjie
    Su, Xiang
    Xi, Chanjuan
    Chen, Hui
    ORGANIC LETTERS, 2014, 16 (14) : 3776 - 3779