Ring expansion of 3-hydroxyoxindoles to 4-quinolones via palladium-catalyzed C-C(acyl) bond cleavage

被引:0
|
作者
Huang, Zhi-Cong [1 ]
Ruan, Zhi-Ling [3 ]
Xu, Hui [1 ]
Dai, Hui-Xiong [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[3] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
FUNCTIONALIZATION; OPTIMIZATION; ACTIVATION; INHIBITORS; AMIDATION; KETONES; ALKYNES;
D O I
10.1039/d4cc05369a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein the construction of 4-quinolones via palladium-catalyzed regioselective beta-acyl elimination of 3-hydroxyoxindoles and a subsequent Camps cyclization process. This protocol is highly efficient and various 4-quinolone derivatives are obtained in high yields. The construction of the core skeleton of the 4-quinolone antibiotics demonstrated the synthetic utility of this method.
引用
收藏
页码:109 / 112
页数:4
相关论文
共 50 条
  • [41] Palladium-Catalyzed C-C Triple Bond Cleavage: Efficient Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones
    Liu, Qilun
    Chen, Pinhong
    Liu, Guosheng
    ACS CATALYSIS, 2013, 3 (02): : 178 - 181
  • [42] Palladium-catalyzed reactions, 3 -: Stereoselective palladium-catalyzed C-C coupling reactions with a diazabicyclo[2.2.1]heptene
    Storsberg, J
    Nandakumar, MV
    Sankaranarayanan, S
    Kaufmann, DE
    ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (02) : 177 - 180
  • [43] Mn(i)-Catalyzed nucleophilic addition/ring expansion via C-H activation and C-C cleavage
    Liu, Bingxian
    Yuan, Yin
    Hu, Panjie
    Zheng, Guangfan
    Bai, Dachang
    Chang, Junbiao
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2019, 55 (72) : 10764 - 10767
  • [44] Palladium-Catalyzed Regioselective C-S Bond Cleavage of Thiophenes
    Huang, Huanan
    Li, Jing
    Lescop, Christophe
    Duan, Zheng
    ORGANIC LETTERS, 2011, 13 (19) : 5252 - 5255
  • [45] Synthesis of N-Substituted 4-Quinolones via Palladium-Catalyzed Enantioselective C-N Coupling and Base-Promoted Reactions
    Pu, Xiaoyun
    Zhang, Yaqi
    He, Xiaobo
    Zhang, Xinhuan
    Jiang, Long
    Cao, Rihui
    Kin Tse, Man
    Qiu, Liqin
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (08) : 1152 - 1157
  • [46] Palladium-Catalyzed Direct Alkoxycarbonylation of Aromatic C-H Bonds via Selective C-C Cleavage of α-Keto Esters
    Zhou, Wei
    Li, Pinhua
    Zhang, Yicheng
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2343 - 2352
  • [47] Rhodium-catalyzed alkenylation of allylbenzenes via C-C bond cleavage
    Kakiuchi, Fumitoshi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [48] Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage
    Gao, Bao
    Huang, Hanmin
    ORGANIC LETTERS, 2017, 19 (22) : 6260 - 6263
  • [49] Kinetic Resolution of Racemic 1-Alkyl-2-methylenecyclopropanes via Palladium-Catalyzed Silaborative C-C Cleavage
    Ohmura, Toshimichi
    Taniguchi, Hiroki
    Suginome, Michinori
    ORGANIC LETTERS, 2009, 11 (13) : 2880 - 2883
  • [50] Palladium-catalyzed selective 2,3-diarylation of α,α-disubstituted 3-thiophenemethanols via cleavage of C-H and C-C bonds
    Nakano, Masaya
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21): : 8309 - 8311