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
来源
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 21期
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
  • [1] Copper-catalyzed asymmetric allylic amination: A novel method for chiral N-aryl allyl amines
    Murru, Siva
    Srivastava, Radhey S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [2] Copper-Catalyzed Rearrangement of N-Aryl Nitrones into Epoxyketimines
    Mo, Dong-Liang
    Anderson, Laura L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (26) : 6722 - 6725
  • [3] Copper-Catalyzed Asymmetric Allylation of N-Aryl Aldimines
    Deng, Yu-Qin
    Yan, Qi-Qi
    Zhang, Ting-Ting
    Zhou, Yi
    He, Cheng-Yu
    Liu, Quan-Zhong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 313 - 320
  • [4] Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides
    Wolter, M
    Klapars, A
    Buchwald, SL
    ORGANIC LETTERS, 2001, 3 (23) : 3803 - 3805
  • [5] Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides
    Panda, Niranjan
    Mothkuri, Raghavender
    Nayak, Dinesh Kumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1602 - 1605
  • [6] Synthesis of triarylamines by copper-catalyzed amination of aryl halides
    Patil, NM
    Kelkar, AA
    Chaudhari, RV
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 223 (1-2) : 45 - 50
  • [7] Synthesis of N-Arylamides by Copper-Catalyzed Amination of Aryl Halides with Nitriles
    Xiang, Shi-Kai
    Zhang, Dong-Xue
    Hu, Hao
    Shi, Jiang-Ling
    Liao, Li-Guo
    Feng, Chun
    Wang, Bi-Qin
    Zhao, Ke-Qing
    Hu, Ping
    Yang, Hua
    Yu, Wen-Hao
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) : 1495 - 1499
  • [8] Regioselective copper-catalyzed amination of chlorobenzoic acids:: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives
    Mei, XF
    August, AT
    Wolf, C
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 142 - 149
  • [9] Copper-catalyzed intramolecular direct amination of sp2 C-H bonds for the synthesis of N-aryl acridones
    Zhou, Wang
    Liu, Yong
    Yang, Youqing
    Deng, Guo-Jun
    CHEMICAL COMMUNICATIONS, 2012, 48 (86) : 10678 - 10680
  • [10] Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines
    Chen, Tengfei
    Chen, Xun
    Wei, Jun
    Lin, Dongen
    Xie, Ying
    Zeng, Wei
    ORGANIC LETTERS, 2016, 18 (09) : 2078 - 2081