-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
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] Microwave-Assisted Synthesis of Benzo[4,5]imidazo[1,2-a ]pyrimidines from -Bromo-,-unsaturated Aldehydes and 2-Aminobenzimidazoles
    Ho, Son Long
    Pham Duy Quang Dao
    Cho, Chan Sik
    SYNLETT, 2017, 28 (14) : 1811 - 1815
  • [22] Exploration of versatile reactions on 2-chloro-3-nitroimidazo[1,2-a]pyridine: expanding structural diversity of C2-and C3-functionalized imidazo[1,2-a]pyridines
    Bazin, Marc-Antoine
    Marhadour, Sophie
    Tonnerre, Alain
    Marchand, Pascal
    TETRAHEDRON LETTERS, 2013, 54 (39) : 5378 - 5382
  • [23] 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
    Fedotov, Victor V.
    Valieva, Maria, I
    Taniya, Olga S.
    Aminov, Semen, V
    Kharitonov, Mikhail A.
    Novikov, Alexander S.
    Kopchuk, Dmitry S.
    Slepukhin, Pavel A.
    Zyryanov, Grigory, V
    Ulomsky, Evgeny N.
    Rusinov, Vladimir L.
    Charushin, Valery N.
    MOLECULES, 2022, 27 (22):
  • [24] One-pot multicomponent synthesis and antimicrobial evaluation of steroidal benzo[4,5]imidazo[1,2-a]pyrimidines with hemolytic assay and molecular docking studies
    Iqbal, Arfeen
    Khan, Asna
    Ahmedi, Saiema
    Mirza, Kainat
    Ali, Abad
    Manzoor, Nikhat
    Siddiqui, Tabassum
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1311
  • [25] A versatile route to 3-(pyrimidin-4-yl)-imidazo[1,2-a]pyridines and 3-(pyrimidin-4-yl)-pyrazolo[1,5-a]pyridines
    Ducray, Richard
    Boutron, Pascal
    Didelot, Myriam
    Germain, Herve
    Lach, Franck
    Lamorlette, Maryannick
    Legriffon, Antoine
    Maudet, Mickael
    Menard, Morgan
    Pasquet, Georges
    Renaud, Fabrice
    Simpson, Iain
    Young, Gail L.
    TETRAHEDRON LETTERS, 2010, 51 (36) : 4755 - 4758
  • [26] Palladium-Catalyzed Double C-H Arylation Reaction: Tandem Synthesis of Benzo[a]imidazo[5,1,2-cd]indolizines from Imidazo[1,2-a]pyridines and o-Dihaloarenes
    Wang, Hanyang
    Chen, Chunxia
    Huang, Zhangjie
    Yao, Liping
    Li, Bin
    Peng, Jinsong
    SYNTHESIS-STUTTGART, 2015, 47 (16): : 2457 - 2466
  • [27] 2-Aryl-3-arylaminoisoxazol-5(2H)-ones as sources of indoles and imidazo[1,2-a]pyridines
    Jeffery, D
    Prager, RH
    Turner, D
    Dreimanis, M
    TETRAHEDRON, 2002, 58 (50) : 9965 - 9972
  • [28] 11H-Benzo[4,5]imidazo[1,2-a]indol-11-one as a New Precursor of Azomethine Ylides: 1,3-Dipolar Cycloaddition Reactions with Cyclopropenes and Maleimides
    Filatov, Alexander S.
    Pronina, Yulia A.
    Selivanov, Stanislav, I
    Shmakov, Stanislav, V
    Uspenski, Anton A.
    Boitsov, Vitali M.
    Stepakov, Alexander, V
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (21)
  • [29] Facile and green method for the synthesis of 4-amino-1,2-dihydrobenzo [4,5]imidazo[1,2-a]pyrimidine-3-carbonitriles catalysed by ammonium acetate
    Hu, Lingjun
    Zhan, Zhajun
    Lei, Min
    Hu, Lihong
    JOURNAL OF CHEMICAL RESEARCH, 2012, (12) : 738 - 739
  • [30] Three-component [3+2+1] cyclizations leading to densely functionalized benzo[4,5]thiazolo[1,2-a]pyrimidines
    Sao, Ming
    Jiang, Bo
    Wang, Haiying
    Li, Liang
    TETRAHEDRON, 2016, 72 (07) : 1011 - 1017