Synthesis of α-Ketone-isoquinoline Derivatives via Tandem Ruthenium(II)-Catalyzed C-H Activation and Annulation

被引:31
|
作者
Wu, Xiao-Lin [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Sichuan, Peoples R China
关键词
PALLADIUM-CATALYZED IMINOANNULATION; AROMATIC KETIMINES; CARDIOTONIC AGENTS; ALKYNES; PYRIDINES; 4-AROYL-1,3-DIHYDRO-2H-IMIDAZOL-2-ONES; BENZYLAMINES; CYCLIZATION; QUINOLINES; ACYLATION;
D O I
10.1021/acs.orglett.8b02759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new ruthenium(II)-catalyzed tandem C-H activation/cyclization/hydrolysis cascade process of 2H-imidazoles and alkynes for facile and regioselective access to alpha-ketone-isoquinolines has been successfully developed. 2H-Imidazole as the novel traceless directing group has been well applied in this paper. The protocol features mild reaction conditions and easily accessible starting materials, and alpha-ketone-isoquinolines could be applied to further construct more complex heterocyclic compounds.
引用
收藏
页码:6990 / 6993
页数:4
相关论文
共 50 条
  • [1] Synthesis of indoles and polycyclic amides via ruthenium(II)-catalyzed C-H activation and annulation
    Lin, Hui
    Li, Shuai-Shuai
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11228 - 11234
  • [2] A ruthenium-catalyzed alkenylation-annulation approach for the synthesis of indazole derivatives via C-H bond activation
    Gholamhosseyni, Maral
    Kianmehr, Ebrahim
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 5973 - 5978
  • [3] Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation
    Yang, Zhenke
    Liu, Jidan
    Li, Yuting
    Ding, Jiawen
    Zheng, Liyao
    Liu, Zhao-Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14809 - 14818
  • [4] Ruthenium(II)-Catalyzed Sterically Hindered C-H Acyloxylation to Synthesize Biaryl Isoquinoline Derivatives via Peresters
    Liu, Hao
    Chi, Wei
    Dong, Lin
    JOURNAL OF PHYSICAL CHEMISTRY C, 2023, 88 (05): : 3148 - 3158
  • [5] Ruthenium(II)-catalyzed N-substituted phthalimide synthesis via C-H activation/[3+2] annulation
    Dong, Xue-Fen
    Fan, Juan
    Shi, Xian-Ying
    Liu, Ke-Yan
    Wang, Peng-Min
    Wei, Jun-Fa
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 779 : 55 - 61
  • [6] Ruthenium(II)-catalyzed C-H activation
    Ackermann, Lutz
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [7] Solvent-Free Ruthenium(II)-Catalyzed C-H Activation: Synthesis of Alkenylarylpyrazole Derivatives
    Shome, Sanchari
    Singh, Surya Prakash
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (27) : 6025 - 6032
  • [8] Ruthenium(II)-catalyzed C-H alkenylation/annulation cascade for the rapid synthesis of benzoimidazoisoindoles
    Selvaraju, Manikandan
    Wang, Ying-Lien
    Sun, Chung-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1358 - 1362
  • [9] Recent Advances in Ruthenium(II)-Catalyzed C-H Bond Activation and Alkyne Annulation Reactions
    Duarah, G.
    Kaishap, P. P.
    Begum, T.
    Gogoi, S.
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) : 654 - 672
  • [10] Synthesis of Polycyclic Amides via Tandem RhIII-Catalyzed C-H Activation and Annulation from Dioxazolones and Alkynes
    Zhang, Guo-Tai
    Dong, Lin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 812 - 816