Direct Synthesis of Disubstituted 3-Isoquinolinone Derivatives through the Construction of C-N, C=O, and C(sp2)-C(sp3) Bonds under Transition-Metal-Free Conditions

被引:11
|
作者
Shi, Jianyi [1 ]
Chen, Xia [1 ]
Huang, Jingyun [1 ]
Lu, Yantong [1 ]
Yang, Zhendong [1 ]
Zhong, Mingli [2 ]
Zhu, Zhongzhi [1 ]
Chen, Xiuwen [1 ]
机构
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China
[2] Guilin Med Univ, Pharmacol Lab Prevent & Treatment High Incidence D, Guilin 541199, Peoples R China
基金
中国国家自然科学基金;
关键词
acetophenone; dearomatization; nitromethane; trifunctionalization; CATALYZED HYDROXYLATION; EFFICIENT SYNTHESIS; ARYL HALIDES; FUNCTIONALIZATION; ISOQUINOLINES; OXIDATION; PHENOLS;
D O I
10.1002/ejoc.202201231
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient three-component cascade coupling reaction of 3-haloisoquinolines, haloalkanes, and sp(3)-carbon nucleophiles (acetophenone or nitromethane) led to a series of structurally novel 1,2-disubstituted-3-isoquinolinones through the formation of C(sp(3))-C(sp(2)), C-N, and C=O bonds. The NaOAc-promoted reaction described in this work is simple to operate, environment friendly, and highly selective.
引用
收藏
页数:5
相关论文
共 50 条
  • [41] C(SP3)-C(SP2) ROTATIONAL BARRIER OF ISOBUTYRAMIDE
    TASAKI, K
    SUTER, UW
    JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (21): : 5886 - 5891
  • [42] Metal-free cascade construction of C-C bonds by activation of inert C(sp3)-H bonds
    Zhang, Honglin
    Pan, Changduo
    Jin, Ning
    Gu, Zhangxi
    Hu, Hongwen
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2015, 51 (07) : 1320 - 1322
  • [43] Electro-organic synthesis of isatins and hydrazones through C-N cross-coupling and C(sp2)-H/C(sp3)-H functionalization
    Verma, Neetu
    Tyagi, Rajdeep
    Khanna, Ashish
    Malviya, Manisha
    Sagar, Ram
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 21 (33) : 6707 - 6714
  • [44] Electro-organic synthesis of isatins and hydrazones through C-N cross-coupling and C(sp2)-H/C(sp3)-H functionalization
    Verma, Neetu
    Tyagi, Rajdeep
    Khanna, Ashish
    Malviya, Manisha
    Sagar, Ram
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (33) : 6707 - 6714
  • [45] On an unusual shortening of the C(sp3)-C(sp3) bonds in n-propylcobaloximes
    Nardin, G
    Randaccio, L
    Tauzher, G
    INORGANICA CHIMICA ACTA, 2000, 299 (02) : 263 - 267
  • [46] Organocatalytic Enantioselective Construction of Conformationally Stable C(sp2)-C(sp3) Atropisomers
    Bertuzzi, Giulio
    Corti, Vasco
    Izzo, Joseph A.
    Ricko, Sebastijan
    Jessen, Nicolaj Inunnguaq
    Jorgensen, Karl Anker
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) : 1056 - 1065
  • [47] Solvent-free aerobic photocatalytic oxidation of C(sp3)-H and C(sp3)-OH to C=O bonds
    Jiang, Xulu
    Wang, Weitao
    Wang, Huan
    He, Zhen-Hong
    Yang, Yang
    Wang, Kuan
    Liu, Zhao-Tie
    Han, Buxing
    GREEN CHEMISTRY, 2024, 26 (08) : 4552 - 4562
  • [48] Access to C(sp3)-C(sp2) and C(sp2)-C(sp2) Bond Formation via Sequential Intermolecular Carbopalladation of Multiple Carbon-Carbon Bonds
    Wen, Yanmei
    Huang, Liangbin
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (12): : 5418 - 5422
  • [50] Mechanism and Origin of Nickel-Catalyzed Decarbonylative Construction of C(sp2)-C(sp3) Bonds from Carboxylic Acids and Their Derivatives
    Tian, Dan-Yan
    Zhao, Wei-Peng
    Xu, Zheng-Yang
    JOURNAL OF ORGANIC CHEMISTRY, 2025,