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
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 61卷 / 01期
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
  • [1] Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones
    Wagner, Cole J.
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [2] Kinetic Resolution of Helicenols via Palladium-Catalyzed Atroposelective C-C Bond Cleavage/Ring-Opening Reaction
    Chen, Zhen
    Yang, Han
    Li, Lin
    Duan, Longhui
    Xi, Junwei
    Gu, Zhenhua
    ORGANIC LETTERS, 2024, 26 (16) : 3429 - 3434
  • [3] Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C-H and C-C Bond Cleavage
    Ano, Yusuke
    Takahashi, Daichi
    Yamada, Yuki
    Chatani, Naoto
    ACS CATALYSIS, 2023, 13 (04) : 2234 - 2239
  • [4] Palladium-Catalyzed Allylic Esterification via C-C Bond Cleavage of a Secondary Homoallyl Alcohol
    Wang, Yong
    Kang, Qiang
    ORGANIC LETTERS, 2014, 16 (16) : 4190 - 4193
  • [5] Palladium-catalyzed kinetic resolution of tert-cyclobutanols via C-C bond cleavage
    Nishimura, T
    Matsumura, S
    Maeda, Y
    Uemura, S
    TETRAHEDRON LETTERS, 2002, 43 (16) : 3037 - 3039
  • [6] Palladium-Catalyzed C-C Bond Formation of Arylhydrazines with Olefins via Carbon-Nitrogen Bond Cleavage
    Zhu, Ming-Kui
    Zhao, Jun-Feng
    Loh, Teck-Peng
    ORGANIC LETTERS, 2011, 13 (23) : 6308 - 6311
  • [7] Palladium-catalyzed C-C bond cleavage of N-cyclopropyl acylhydrazones
    Fujioka, Hiroki
    Yasui, Motohiro
    Hamada, Shohei
    Fukumi, Kohei
    Takeda, Norihiko
    Kobayashi, Yusuke
    Furuta, Takumi
    Ueda, Masafumi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (16) : 3262 - 3267
  • [8] Palladium-catalyzed transformation of cyclobutanone O-benzoyloximes to nitriles via C-C bond cleavage
    Nishimura, T
    Nishiguchi, Y
    Maeda, Y
    Uemura, S
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16): : 5342 - 5347
  • [9] Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond cleavage under oxygen atmosphere
    Nishimura, T
    Araki, H
    Maeda, Y
    Uemura, S
    ORGANIC LETTERS, 2003, 5 (17) : 2997 - 2999
  • [10] Intramolecular cycloisomerization of a propanes via NHC palladium-catalyzed cascade C-C bond cleavage/C-H activation/C-C bond formation
    Yang, Yewei
    Huang, Xian
    SYNLETT, 2008, (09) : 1366 - 1370
12345