Palladium-catalyzed intermolecular oxidative cyclization of N-aryl enamines with isocyanides through double sp2 C-H bonds cleavage: facile synthesis of 4-aminoquinoline derivatives

被引:25
|
作者
Zheng, Qiang [1 ,2 ]
Luo, Puying [3 ]
Lin, Yuqing [1 ,2 ]
Chen, Wenfan [1 ,2 ]
Liu, Xiuxiu [1 ,2 ]
Zhang, Yadong [1 ,2 ]
Ding, Qiuping [1 ,2 ]
机构
[1] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
[3] Jiangxi Prov Peoples Hosp, Dept Obstet & Gynecol, Nanchang 330006, Jiangxi, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; QUINOLINE DERIVATIVES; VERSATILE SYNTHESIS; EFFICIENT SYNTHESIS; ANTI-HIV-1; AGENTS; CASCADE REACTIONS; INSERTION; ACTIVATION; PYRROLES; INDOLES;
D O I
10.1039/c5ob00329f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of 4-aminoquinolines via palladium-catalyzed intermolecular oxidative cyclization of N-aryl enamines and isocyanides through double sp(2) C-H bonds cleavage has been developed.
引用
收藏
页码:4657 / 4660
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Intermolecular Oxidative Coupling Reactions of (Z)-Enamines with Isocyanides through Selective -C(sp2)-H and/or C=C Bond Cleavage
    Hu, Weigao
    Zheng, Jia
    Li, Meng
    Wu, Wanqing
    Liu, Haiyang
    Jiang, Huanfeng
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (08) : 712 - 715
  • [2] New palladium-catalyzed aerobic oxidative cleavage and cyclization of N-aryl peptide derivatives
    El Kaim, Laurent
    Gamez-Montano, Rocio
    Grimaud, Laurence
    Ibarra-Rivera, Tannya
    CHEMICAL COMMUNICATIONS, 2008, (11) : 1350 - 1352
  • [3] Palladium-Catalyzed Intramolecular Amidation of C(sp2)-H Bonds: Synthesis of 4-Aryl-2-quinolinones
    Inamoto, Kiyofumi
    Saito, Tadataka
    Hiroya, Kou
    Doi, Takayuki
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11): : 3900 - 3903
  • [4] Copper-catalyzed intramolecular direct amination of sp2 C-H bonds for the synthesis of N-aryl acridones
    Zhou, Wang
    Liu, Yong
    Yang, Youqing
    Deng, Guo-Jun
    CHEMICAL COMMUNICATIONS, 2012, 48 (86) : 10678 - 10680
  • [5] Synthesis of isatins by the palladium-catalyzed intramolecular acylation of unactivated aryl C(sp2)-H bonds
    Li, Jue
    Zheng, Yang
    Yu, Xinling
    Lv, Songyang
    Wang, Qiantao
    Hai, Li
    Wu, Yong
    RSC ADVANCES, 2015, 5 (125) : 103280 - 103283
  • [6] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes
    Basle, Olivier
    Bidange, Johan
    Shuai, Qi
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1145 - 1149
  • [7] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Alcohols
    Xiao, Fuhong
    Qi Shuai
    Zhao, Feng
    Basle, Olivier
    Deng, Guojun
    Li, Chao-Jun
    ORGANIC LETTERS, 2011, 13 (07) : 1614 - 1617
  • [8] Synthesis of Heteroarylated Polyfluorobiphenyls via Palladium-Catalyzed Sequential sp2 C-H Bonds Functionalizations
    Yan, Tao
    Chen, Lu
    Bruneau, Christian
    Dixneuf, Pierre H.
    Doucet, Henri
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 4177 - 4183
  • [9] Palladium-Catalyzed Intramolecular Oxidative Coupling Involving Double C(sp2)-H Bonds for the Synthesis of Annulated Biaryl Sultams
    Laha, Joydev K.
    Jethava, Krupal P.
    Dayal, Neetu
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8010 - 8019
  • [10] Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion
    Thu, Hung-Yat
    Yu, Wing-Yiu
    Che, Chi-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) : 9048 - 9049