Copper-Catalyzed Cascade Amination Route to N-Aryl Benzimidazoquinazolinones

被引:27
作者
Banerjee, Arpan [1 ]
Subramanian, Parthasarathi [1 ]
Kaliappan, Krishna P. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
C-H AMINATION; ONE-POT; BOND FORMATION; KINASE INHIBITORS; DERIVATIVES; ACTIVATION; EFFICIENT; HETEROARYL; AMIDATION; CLEAVAGE;
D O I
10.1021/acs.joc.6b01287
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot Cu-catalyzed C-H functionalization/two-fold C-N bond formation protocol for the syntheses of N-aryl benzimidazoquinazolinones is being reported. This strategy involves a Cu-catalyzed C-N bond coupling reaction between N-anilinoquinazolinones and aryl/heteroaryl halides followed by acetate ligand-assisted intramolecular C-H amination.(1a) This reaction is high-yielding and straightforward for the synthesis of anti-cancer drug analogues of benzimidazoquinazolinones.
引用
收藏
页码:10424 / 10432
页数:9
相关论文
共 50 条
  • [21] A simple and efficient copper-catalyzed amination of aryl halides by aqueous ammonia in water
    Zhu, Yefeng
    Wei, Yunyang
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2011, 89 (06): : 645 - 649
  • [22] Copper-catalyzed arenes amination with saccharins
    Sun, Kai
    Li, Yan
    Zhang, Qian
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1354 - 1358
  • [23] A Synthetic Approach to N-Aryl Carbamates via Copper-Catalyzed Chan-Lam Coupling at Room Temperature
    Moon, Soo-Yeon
    Kim, U. Bin
    Sung, Dan-Bi
    Kim, Won-Suk
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) : 1856 - 1865
  • [24] Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines
    Matsuda, Naoki
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ORGANIC LETTERS, 2011, 13 (11) : 2860 - 2863
  • [25] Copper-Catalyzed Multicomponent Coupling Reaction of Primary Aromatic Amines, Rongalite, and Alkynes: Access to N-Aryl Propargylamines
    Wang, Miao
    Ren, Hui-Ying
    Zhang, Xiao-Lu
    Pu, Xiao-Yu
    Jiang, Shan
    Zhao, Bang-Tun
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11) : 8220 - 8229
  • [26] Copper-catalyzed oxidative amination of methanol to access quinazolines
    Satish, Gandhesiri
    Polu, Ashok
    Kota, Laxman
    Ilangovan, Andivelu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4774 - 4782
  • [27] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [28] Palladium-catalyzed aerobic oxidative C-H amination: synthesis of 2-unsubstituted and 2-substituted N-aryl benzimidazoles
    Kumar, Rapolu Kiran
    Punniyamurthy, Tharmalingam
    RSC ADVANCES, 2012, 2 (11): : 4616 - 4619
  • [29] Fe-catalyzed synthesis of substituted N-aryl oxazolidines
    Murru, Siva
    Lott, Charles Seth
    McGough, Brandon
    Bernard, Dakota M.
    Srivastava, Radhey S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (15) : 3681 - 3685
  • [30] Copper-catalyzed cascade C-N coupling/C-H amination: one pot synthesis of imidazo[1,2-b]indazole
    Rajesham, Bandari
    Arunkumar, Vemula
    Naikawadi, Praveen Kumar
    Kumar, K. Shiva
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (37) : 15816 - 15820