-Perfluoroalkyl Peroxides as Fluorinated C3-Building Blocks for the Construction of Benzo[4,5]imidazo[1,2-a]pyridines

被引:6
|
作者
Ma, Yangyang [1 ]
Lv, Leiyang [1 ]
Li, Zhiping [1 ]
机构
[1] Renmin Univ China, Dept Chem, Key Lab Adv Light Convers Mat & Biophoton, Beijing 100872, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 02期
基金
中国国家自然科学基金;
关键词
CATALYZED CARBONYLATION-PEROXIDATION; TRIFLUOROMETHYLATION; ANNULATION; DERIVATIVES; STYRENES; INDOLES; ARENES; BENZO;
D O I
10.1021/acs.joc.1c02589
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and selective protocol for the synthesis of perfluoroalkyl-group-substituted benzo[4,5]imidazo[1,2-a]-pyridines has been developed in which beta-perfluoroalkyl peroxides act as novel fluorinated C3-building blocks to implement regioselective [3 + 3] annulation with 2-cyanomethyl benzimidazole under metal-free conditions. The application of the synthesized perfluoroalkylated BIPs as potent anticancer reagents versus the nonfluorinated ones demonstrated the biological utility of this method.
引用
收藏
页码:1564 / 1573
页数:10
相关论文
共 50 条
  • [21] Synthesis of Benzo[4,5]imidazo[1,2-a]naphthyridine and Benzo[4,5]imidazo[2,1-a]isoquinoline Derivatives Catalyzed by CuI/L-Proline
    Dong, Fang
    Pan, Wan-Chen
    Liu, Jian-Quan
    Wang, Xiang-Shan
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (02) : 465 - 474
  • [22] An Efficient Synthesis of Pyrrolo[1,2-a] or Pyrido[1,2-a]benzo[4,5]imidazo[1,2-c]quinazoline Derivatives in Ionic Liquids Catalyzed by Iodine
    Wang, Yue
    Liu, Jian-Quan
    Wang, Xiang-Shan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3440 - 3446
  • [23] Synthesis of Indeno[1′,2′:4,5]imidazo[1,2-a]pyridin-11-ones and Chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-ones through Palladium-Catalyzed Cascade Reactions of 2-(2-Bromophenyl)imidazo[1,2-a]pyridines
    Zhang, Ju
    Zhang, Xinying
    Fan, Xuesen
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08): : 3206 - 3213
  • [24] Transition-metal-free C-N and C-C formation: synthesis of benzo[4,5] imidazo[1,2-a] pyridines and 2-pyridones from ynones
    Teng, Qing-Hu
    Peng, Xiang-Jun
    Mo, Zu-Yu
    Xu, Yan-Li
    Tang, Hai-Tao
    Wang, Heng-Shan
    Sun, Hong-Bin
    Pan, Ying-Ming
    GREEN CHEMISTRY, 2018, 20 (09) : 2007 - 2012
  • [25] 2-Trifluoromethyl-10H-benzo[4,5]imidazo[1,2-a] pyrimidin-4-one
    Chandra
    Puttaraju, K. B.
    Shivashankar, K.
    Babu, E. A. Jithesh
    Mahendra, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1536 - +
  • [26] Reaction of imidazo[1,2-a]pyridines with aliphatic aldehydes: A simple and efficient method for the preparation of novel c-3 vinylic derivatives of imidazo[1,2-a]pyridines
    Zhang, Rui
    Hu, Yongzhou
    SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 377 - 389
  • [27] One-pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyridine Derivatives in Aqueous Conditions
    Vodolazhenko, Maria A.
    Mykhailenko, Anastasiia E.
    Gorobets, Nikolay Yu.
    Desenko, Sergey M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 753 - 757
  • [28] Au(I)/Ag(I)-Catalyzed Cascade Approach for the Synthesis of Benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinones
    Ji, Xun
    Zhou, Yu
    Wang, Jinfang
    Zhao, Linxiang
    Jiang, Hualiang
    Liu, Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09): : 4312 - 4318
  • [29] Synthesis of benzo[4,5]imidazo[1,2-a]quinoxalines by I2-mediated sp3 C-H amination
    Chen, Wenjun
    Du, Yangxu
    Wang, Manman
    Fang, Yingchao
    Yu, Wenquan
    Chang, Junbiao
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (22) : 3705 - 3708
  • [30] Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid
    Yang, Kai
    Luo, Shi-He
    Chen, Si-Hong
    Cao, Xi-Ying
    Zhou, Yong-Jun
    Lin, Yan-Lan
    Huo, Yan-Ping
    Wang, Zhao-Yang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (37) : 8133 - 8139