CBr4-Promoted Efficient Synthesis of 2-(1H-Benzo[d]imidazol-2-yl)-3-arylacrylonitriles

被引:2
|
作者
Wang, Xiang [1 ]
Chen, Ping [1 ]
Zhi, Sanjun [1 ]
Hu, Huayou [1 ]
Kan, Yuhe [1 ]
机构
[1] Huaiyin Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Chem Low Dimens Mat, Huaian 223300, Peoples R China
基金
中国国家自然科学基金;
关键词
benzimidazol; carbon tetrabromide; acrylonitrilel; Knoevenagel condensation; KNOEVENAGEL CONDENSATION; IN-VITRO; BENZIMIDAZOLES; INHIBITORS;
D O I
10.6023/cjoc201804037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(1H-Benzo[d]imidazol-2-yl)-3-arylacrylonitrile derivatives not only exhibit a variety of important biological activities, but also are important intermediates in organic synthesis. The CBr4-promoted reaction of aromatic aldehydes with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile to obtain 2-(1H-benzo[d]imidazol-2-yl)-3-arylacrylonitriles was developed. Structurally diverse 2-(1H-benzo[d]imidazol-2-yl)-3-anlacrylonitriles were obtained in moderate to good yields (74%-96%) under mild conditions. This method has the advantages of operational simplicity and wide substrate scope.
引用
收藏
页码:3123 / 3126
页数:4
相关论文
共 23 条
  • [1] Babu P. N. K., 2013, CHEM SIN, V4, P107
  • [2] High Performance Exciplex-Based Fluorescence-Phosphorescence White Organic Light-Emitting Device with Highly Simplified Structure
    Chen, Zhan
    Liu, Xiao-Ke
    Zheng, Cai-Jun
    Ye, Jun
    Liu, Chuan-Lin
    Li, Fan
    Ou, Xue-Mei
    Lee, Chun-Sing
    Zhang, Xiao-Hong
    [J]. CHEMISTRY OF MATERIALS, 2015, 27 (15) : 5206 - 5211
  • [3] Dubey PK, 2007, INDIAN J HETEROCY CH, V16, P395
  • [4] Gao X., 2015, ASIAN J CHEM, V27, P2145, DOI [10.14233/ajchem.2015.17821, DOI 10.14233/AJCHEM.2015.17821]
  • [5] Discovery of novel Benzimidazoles as potent inhibitors of TIE-2 and VEGFR-2 tyrosine kinase receptors
    Hasegawa, Masaichi
    Nishigaki, Naohiko
    Washio, Yoshiaki
    Kano, Kazuya
    Harris, Philip A.
    Sato, Hideyuki
    Mori, Ichiro
    West, Rob I.
    Shibahara, Megumi
    Toyoda, Hiroko
    Wang, Liping
    Nolte, Robert T.
    Veal, James M.
    Cheung, Mui
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (18) : 4453 - 4470
  • [6] Hou H., 2014, CHINESE J ORG CHEM, V1277, P34
  • [7] Synthesis of novel benzimidazolyl-substituted acrylonitriles and amidino-substituted enzimidazo[1,2-a]quinolines
    Hranjec, Marijana
    Karminski-Zamola, Grace
    [J]. MOLECULES, 2007, 12 (08) : 1817 - 1828
  • [8] Benzimidazole derivatives related to 2,3-acrylonitriles, benzimidazo[1,2-a]quinolines and fluorenes: Synthesis, antitumor evaluation in vitro and crystal structure determination
    Hranjec, Marijana
    Pavlovic, Gordana
    Marjanovic, Marko
    Kralj, Marijeta
    Karminski-Zamola, Grace
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (06) : 2405 - 2417
  • [9] Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence
    Hsu, Wei-Shun
    Tsai, Min-Huan
    Barve, Indrajeet J.
    Yellol, Gorakh S.
    Sun, Chung-Ming
    [J]. ACS COMBINATORIAL SCIENCE, 2017, 19 (07) : 492 - 499
  • [10] CBr4 as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones
    Kazi, Imran
    Guha, Somraj
    Sekar, Govindasamy
    [J]. ORGANIC LETTERS, 2017, 19 (05) : 1244 - 1247