Auto-tandem catalysis:: Synthesis of substituted 11H-indolo [3,2-c]quinolines via palladium-catalyzed intermolecular C-N and intramolecular C-C bond formation

被引：62
|
作者：
Meyers, Caroline [1 ]
Rornbouts, Geert [1 ]
Loones, Kristof T. J. [1 ]
Coelho, Alberto [1 ]
Maes, Bert U. W. [1 ]
机构：
[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 03期
关键词：
amination; C-H activation; malaria; palladium; tandem catalysis;
D O I：
10.1002/adsc.200700328
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
D-Ring substituted 11H-indolo[3,2-c]quinolines (4) have been prepared via auto-tandem consecutive intermolecular Buchwald-Hartwig reaction and intramolecular palladium-catalyzed arylation on 4-chloroquinoline (1) with N-unsubstituted 2-chloroanilines (2). The reported 11H-indolo[3,2-c]quinolines (4) represent the first examples in which tandem catalysis has been used to construct N-unsubstituted carbolines.
引用
收藏
页码：465 / 470
页数：6
相关论文
共 50 条
  • [1] Convenient Synthesis of 11-Substituted 11H-Indolo[3,2-c]quinolines by Sequential Chemoselective Suzuki Reaction/Double C-N Coupling
    Ngo Nghia Pham
    Janke, Sophie
    Salman, Ghazwan Ali
    Tuan Thanh Dang
    Thanh Son Le
    Spannenberg, Anke
    Ehlers, Peter
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (37) : 5554 - 5565
  • [2] A CONVENIENT SYNTHESIS OF 11H-INDOLO [3,2-C] QUINOLONES
    STADLBAUER, W
    KAREM, AS
    KAPPE, T
    MONATSHEFTE FUR CHEMIE, 1987, 118 (01): : 81 - 89
  • [3] Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation
    Tsang, W. C. Peter
    Munday, Rachel H.
    Brasche, Gordon
    Zheng, Nan
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7603 - 7610
  • [4] Palladium-Catalyzed Synthesis of 1-Alkyl-5-Arylpyrazoles: The Auto-Tandem Catalysis for C-C Bond Cleavage/Heck Arylation
    Fujioka, Hiroki
    Yasui, Motohiro
    Hamada, Shohei
    Takeda, Norihiko
    Kobayashi, Yusuke
    Furuta, Takumi
    Ueda, Masafumi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (09)
  • [5] Assembly of Substituted 2-Alkylquinolines by a Sequential Palladium-Catalyzed C-N and C-C Bond Formation
    Matsubara, Yoshio
    Hirakawa, Saori
    Yamaguchi, Yoshihiro
    Yoshida, Zen-ichi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7670 - 7673
  • [6] Palladium-catalyzed domino intramolecular N-arylation/intermolecular C-C bond formation for the synthesis of functionalized benzodiazepinediones
    Salcedo, Angela
    Neuville, Luc
    Rondot, Christophe
    Retailleau, Pascal
    Zhu, Jieping
    ORGANIC LETTERS, 2008, 10 (05) : 857 - 860
  • [7] Straightforward synthesis of 11H-indolo[3,2-c]isoquinoline and benzofuro[3,2-c]isoquinoline by ring transformation
    Béres, M
    Timári, G
    Hajós, G
    TETRAHEDRON LETTERS, 2002, 43 (34) : 6035 - 6038
  • [8] Regiodivergent Synthesis of 11H-Indolo[3,2-c]quinolines and Neocryptolepine from a Common Starting Material
    Haheim, Katja S.
    Lund, Bjarte Aarmo
    Sydnes, Magne O.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (13)
  • [9] Palladium-Catalyzed intramolecular C-H Activation/C-C Bond Formation: A Straightforward Synthesis of Phenanthridines
    Peng, Jinsong
    Chen, Tonghui
    Chen, Chunxia
    Li, Bin
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22): : 9507 - 9513
  • [10] A Direct Palladium-Catalyzed Route to Selectively Substituted Carbazoles through Sequential C-C and C-N Bond Formation: Synthesis of Carbazomycin A
    Della Ca, Nicola
    Sassi, Giovanni
    Catellani, Marta
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2179 - 2182
12345