Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C-H/N-O bond activation

被引:13
|
作者
Lin, Wei [1 ]
Hu, Xiu-Xiu [1 ]
Zhuang, Cang-Wei [1 ]
Wang, Ya-Zhen [1 ]
机构
[1] Jiangsu Univ Technol, Sch Chem & Environm Engn, Changzhou 213001, Peoples R China
关键词
Isoquinoline; Synthesis; Cyclization; Iridium(III)-catalysis; H FUNCTIONALIZATION; BETA-PHENYLETHYLAMINES; DIRECTING GROUPS; 4+2 ANNULATION; N-OXIDE; AMIDATION; OXIMES; ALKYNYLATION; HETEROCYCLES; CYCLIZATION;
D O I
10.1016/j.tet.2019.04.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient approach to synthesize isoquinoline derivatives through Iridium(III)-catalyzed cyclization of aryl ketoximes and internal alkynes without oxidant is reported. A broad range isoquinolines are obtained in good to excellent yields and various functional groups are well tolerated. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3015 / 3023
页数:9
相关论文
共 50 条
  • [1] Easy Access to Isoquinolines and Tetrahydroquinolines from Ketoximes and Alkynes via Rhodium-Catalyzed C-H Bond Activation
    Parthasarathy, Kanniyappan
    Cheng, Chien-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9359 - 9364
  • [2] Easy Access to 1-Amino and 1-Carbon Substituted Isoquinolines via Cobalt-Catalyzed C-H/N-O Bond Activation
    Muralirajan, Krishnamoorthy
    Kuppusamy, Ramajayam
    Prakash, Sekar
    Cheng, Chien-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (05) : 774 - 783
  • [3] Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines
    Chinnagolla, Ravi Kiran
    Pimparkar, Sandeep
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2012, 14 (12) : 3032 - 3035
  • [4] Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation
    Sivakumar, Ganesan
    Vijeta, Arjun
    Jeganmohan, Masilamani
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (17) : 5899 - 5903
  • [5] C-H amination via N-O activation
    Seveney, Lauren
    Oppong, Anita
    DeBoef, Brenton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [6] Synthesis of Isoquinolines from Benzimidates and Alkynes via Cobalt(III)-Catalyzed C-H Functionalization/Cyclization
    Gong, Shasha
    Xi, Wanlin
    Ding, Zhenhua
    Sun, Haiying
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14): : 7643 - 7647
  • [7] Iridium-Catalyzed Hydroarylation via C-H Bond Activation
    Nishimura, Takahiro
    CHEMICAL RECORD, 2021, 21 (12): : 3532 - 3545
  • [8] Rhodium(III)-catalyzed annulation of arenes with alkynes assisted by an internal oxidizing N-O bond
    Qi, Zisong
    Tang, Guo-Dong
    Pan, Cheng-Ling
    Li, Xingwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (45) : 10977 - 10980
  • [9] Access to 2-Aroylthienothiazoles via C-H/N-O Bond Functionalization of Oximes
    Zhou, Peiqi
    Huang, Yubing
    Wu, Wanqing
    Zhou, Jiaming
    Yu, Wentao
    Jiang, Huanfeng
    ORGANIC LETTERS, 2019, 21 (24) : 9976 - 9980
  • [10] Synthesis of Pyridines from Ketoximes and Terminal Alkynes via C-H Bond Functionalization
    Martin, Rhia M.
    Bergman, Robert G.
    Ellman, Jonathan A.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (05): : 2501 - 2507