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
  • [31] Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations
    Wu, Jiamin
    Zhang, Jinli
    Jiao, Yongjuan
    Deng, Gongtao
    Li, Yingmei
    Zhang, Zhengyu
    Jiang, Yaojia
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17462 - 17470
  • [32] Palladium-catalyzed C-C bond formation from β-chloroacroleins in aqueous media
    Hesse, S
    Kirsch, G
    SYNTHESIS-STUTTGART, 2001, (05): : 755 - 758
  • [33] Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C-C bond activation
    Pan, Dong
    Chen, Gen-Qiang
    Tang, Xiang-Ying
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (07): : 792 - 796
  • [34] Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts
    He, Yuan
    Huang, Zilong
    Ma, Juan
    Huang, Fei
    Lin, Jie
    Wang, Hongmei
    Xu, Bao-Hua
    Zhou, Yong-Gui
    Yu, Zhengkun
    ORGANIC LETTERS, 2021, 23 (15) : 6110 - 6114
  • [35] Palladium-catalyzed decarboxylative C-C bond formation of secondary benzyl electrophiles
    Mendis, Shehani
    Tunge, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [36] Palladium-Catalyzed Arylation of Olefins by Triarylphosphines via C-P Bond Cleavage
    Lu, Dapeng
    Xu, Yu
    Liu, Wenjing
    Guo, Lijuan
    Sun, Xingxia
    HELVETICA CHIMICA ACTA, 2015, 98 (01) : 116 - 122
  • [37] Direct C-3-Alkenylation of Quinolones via Palladium-Catalyzed C-H Functionalization
    Li, Mingzong
    Li, Liangxi
    Ge, Haibo
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2445 - 2449
  • [38] EXAMPLE OF THERMODYNAMIC CONTROL IN PALLADIUM-CATALYZED ALLYLIC ALKYLATION - EVIDENCE FOR PALLADIUM-ASSISTED ALLYLIC C-C BOND-CLEAVAGE
    NILSSON, YIM
    ANDERSSON, PG
    BACKVALL, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 6609 - 6613
  • [39] Palladium-catalyzed selective C-C bond cleavage of keto-vinylidenecyclopropanes: construction of structurally rich dihydrofurans and tetrahydrofurans
    Ning, Chao
    Yu, Ziqi
    Shi, Min
    Wei, Yin
    CHEMICAL SCIENCE, 2024, 15 (24) : 9192 - 9200
  • [40] PALLADIUM-CATALYZED SEQUENTIAL INSERTION OF DOUBLE-BONDS FOLLOWED BY BETA,GAMMA-CLEAVAGE OF A C-C BOND
    CATELLANI, M
    CHIUSOLI, GP
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 247 (03) : C59 - C62