Cross-coupling of 2-methylquinolines and in-situ activated isoquinolines: Construction of 1,2-disubstituted isoquinolinones

被引:0
|
作者
Jianyi Shi [1 ]
Zheng Zeng [2 ]
Shengting Xu [1 ]
Zechun Cai [1 ]
Yuehua Luo [1 ]
Yongbo Fan [1 ]
Zhongzhi Zhu [1 ]
Tingting Wen [1 ]
Xiuwen Chen [1 ]
机构
[1] School of Biotechnology and Health Sciences, Wuyi University
[2] Affiliated Hospital of Guilin Medical University
基金
中国国家自然科学基金;
关键词
D O I
暂无
中图分类号
O626.323 [];
学科分类号
070303 ; 081704 ;
摘要
In this study,a method was developed to form C(sp~3)-C(sp~2) bonds via copper catalyst-promoted cross coupling of 2-methylquinoline and in-situ-activated 3-haloisoquinoline under mild conditions.The multicomponent tandem reaction was used to construct new C-N,C=O and C-C bonds in one pot via sequential functionalization of the N1,C3 and C1 positions of 3-haloisoquinoline.This method can be used to efficiently access 1,2-disubstituted isoquinolinones by the three-component reaction of 3-halogen isoquinoline,alkyl halide,and 2-methylquinoline.
引用
收藏
页码:4874 / 4877
页数:4
相关论文
共 50 条
  • [1] Cross-coupling of 2-methylquinolines and in-situ activated isoquinolines: Construction of 1,2-disubstituted isoquinolinones
    Shi, Jianyi
    Zeng, Zheng
    Xu, Shengting
    Cai, Zechun
    Luo, Yuehua
    Fan, Yongbo
    Zhu, Zhongzhi
    Wen, Tingting
    Chen, Xiuwen
    CHINESE CHEMICAL LETTERS, 2022, 33 (11) : 4874 - 4877
  • [2] Synthesis of 1,2-disubstituted imidazoles via cross-coupling and substitution reactions
    Langhammer, I
    Erker, T
    HETEROCYCLES, 2005, 65 (11) : 2721 - 2728
  • [3] Stereoselective synthesis of (E)-1,2-disubstituted ethenes by means of sequential cross-coupling reactions
    Zhu, LS
    Huang, XA
    SYNTHETIC COMMUNICATIONS, 1997, 27 (01) : 39 - 44
  • [5] Synthesis of 1,2-Disubstituted Cyclopentadienes from Alkynes Using a Catalytic Haloallylation/Cross-Coupling/Metathesis Relay
    Topolovcan, Nikola
    Panov, Illia
    Kotora, Martin
    ORGANIC LETTERS, 2016, 18 (15) : 3634 - 3637
  • [6] One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes
    Arkhypchuk, Anna I.
    D'Imperio, Nicolas
    Ott, Sascha
    ORGANIC LETTERS, 2018, 20 (17) : 5086 - 5089
  • [7] Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organoalane reagents
    Shao, Xue-Bei
    Jiang, Xin
    Li, Qing-Han
    Zhao, Zhi-Gang
    TETRAHEDRON, 2018, 74 (41) : 6063 - 6070
  • [8] Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents
    Wu, Chuan
    Li, Qing-Han
    TETRAHEDRON, 2021, 96
  • [9] Multicomponent Cyclizative 1,2-Rearrangement Enabled Enantioselective Construction of 2,2-Disubstituted Pyrrolinones
    Li, Xing-Zi
    He, Yu-Ping
    Wu, Hua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (07)
  • [10] Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki-Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation
    Schumacher, Andreas
    Schrems, Marcus G.
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) : 13502 - 13509