Modular Synthesis of Quinazolinone-Fused Phenanthridinones by a Palladium-Catalyzed Cascade C-H/N-H Arylation Process

被引：15
|
作者：
Yu, Yanhan [1 ]
Yue, Yixia [1 ]
Wang, Deqiang [1 ]
Li, Xue [1 ]
Chen, Chunxia [1 ]
Peng, Jinsong [1 ]
机构：
[1] Northeast Forestry Univ, Coll Sci, Dept Chem & Chem Engn, Harbin 150040, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 22期
基金：
中国国家自然科学基金;
关键词：
palladium; C-H arylation; amidation; tandem reactions; ring-fused quinazolinones; DOMINO SYNTHESIS; BOND FORMATION; AMINATION; 2-ARYLBENZIMIDAZOLES; CHEMISTRY; BROMIDES;
D O I：
10.1055/s-0035-1561481
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient palladium-catalyzed protocol for the tandem synthesis of quinazolinone-fused phenanthridinones from 2-aryl-quinazolinones and o-dihaloarenes is described. This reaction sequence comprises direct intermolecular C-H arylation of 2-arylquinazolinones followed by an intramolecular aryl amidation reaction, affording 14Hquinazolino[3,2-f] phenanthridin-14-one derivatives in moderate to good yields.
引用
收藏
页码：3941 / 3950
页数：10
相关论文
共 50 条
  • [21] Palladium-Catalyzed C-H Arylation of Amides by Triazole Assistance
    Santrac, Darko
    Cella, Stefano
    Wang, Wei
    Ackermann, Lutz
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (32) : 5429 - 5436
  • [22] Palladium-Catalyzed Oxidative Cycloaddition through C-H/N-H Activation: Access to Benzazepines
    Wang, Lei
    Huang, Jiayao
    Peng, Shiyong
    Liu, Hui
    Jiang, Xuefeng
    Wang, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) : 1768 - 1772
  • [23] Synthesis of fused aromatic heterocycles by palladium-catalyzed C-H activation chemistry
    Pacheco, Jarren
    Knoerzer, Timm
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [24] Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides:: Application to the synthesis of (±)-anabasine
    Larivee, Alexandre
    Mousseau, James J.
    Charette, Andre B.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) : 52 - +
  • [25] SYNTHESIS OF PHENANTHRIDINES AND RELATED COMPOUNDS BY PALLADIUM-CATALYZED DIRECT COUPLING VIA C-H AND N-H BOND CLEAVAGES
    Takeda, Daisuke
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    HETEROCYCLES, 2012, 86 (01) : 487 - 496
  • [26] Palladium-Catalyzed Modular Synthesis of Thiophene-Fused Polycyclic Aromatics via Sequential C-H Activation
    Fu, Ying
    Chen, Hao
    Liu, Jiajia
    Luo, Yu
    Chen, Dongping
    Du, Zhengyin
    ORGANIC LETTERS, 2025, 27 (05) : 1142 - 1146
  • [27] Palladium-catalyzed direct C2-arylation of free (N-H) indoles via norbornene-mediated regioselective C-H activation
    Gao, Yadong
    Zhu, Wangying
    Yin, Long
    Dong, Bo
    Fu, Jingjing
    Ye, Zhiwen
    Xue, Fengtian
    Jiang, Chao
    TETRAHEDRON LETTERS, 2017, 58 (23) : 2213 - 2216
  • [28] Palladium-Catalyzed Oxidative Annulation via C-H/N-H Functionalization: Access to Substituted Pyrroles
    Peng, Shiyong
    Wang, Lei
    Huang, Jiayao
    Sun, Shaofa
    Guo, Haibing
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2550 - 2557
  • [29] Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes
    Broggini, Gianluigi
    Beccalli, Egle M.
    Fasana, Andrea
    Gazzola, Silvia
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1730 - 1746
  • [30] Palladium-Catalyzed Decarboxylative Arylation of C-H Bonds by Aryl Acylperoxides
    Yu, Wing-Yiu
    Sit, Wing Nga
    Zhou, Zhongyuan
    Chan, Albert S. -C.
    ORGANIC LETTERS, 2009, 11 (15) : 3174 - 3177
12345