One-pot synthesis of 2,4,5-trisubstituted-1H-imidazoles promoted by nano-TiCl4 • SiO2: An experimental and theoretical study

被引:0
作者
Zamani, Leila [1 ]
Mirjalili, Bi Bi Fatemeh [1 ]
Namazian, Mansoor [1 ]
机构
[1] Yazd Univ, Dept Chem, Yazd, Iran
来源
CHEMIJA | 2013年 / 24卷 / 04期
关键词
2,4,5-tri-substituted-1H-imidazoles; nano-TiCl4 center dot SiO2; benzil; solvent-free conditions; ab initio; SUBSTITUTED IMIDAZOLES; EFFICIENT CATALYST; CONDENSATION; TRIFLATE; ANALOGS; SYSTEM;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nano-TiCl4 center dot SiO2 has been found to be an extremely efficient catalyst for the preparation of 2,4,5-trisubstituted imidazoles via three-component reactions of benzil, aldehydes and ammonium acetate under mild conditions. Nano-TiCl4 center dot SiO2 as a solid Lewis acid has been synthesized by reaction of nano-SiO2 and TiCl4. The structure characterization of this acid has been studied by XRD, SEM and TEM. This process was simple and environmentally benign with high to excellent yields. Furthermore, the catalyst could be recovered conveniently and reused for at least three times. Standard ab initio calculations have been carried out in order to identify the possible reaction mechanism.
引用
收藏
页码:312 / 319
页数:8
相关论文
共 50 条
  • [41] PEG-400 as an efficient reaction medium for the synthesis of 2,4,5-triaryl-1H-imidazoles and 1,2,4,5-tetraaryl-1H-imidazoles
    Wang, Xi Cun
    Gong, Hai Peng
    Quan, Zheng Jun
    Li, Lei
    Ye, He Lin
    CHINESE CHEMICAL LETTERS, 2009, 20 (01) : 44 - 47
  • [42] A Fast, Highly Efficient and Green Protocol for One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Catalyzed by [TBA]2[W6O19] as a Reusable Heterogeneous Catalyst
    Ashrafi, Mozhgan
    Davoodnia, Abolghasem
    Tavakoli-Hoseini, Niloofar
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (05) : 1508 - 1512
  • [43] A greener route for the one-pot synthesis of 1,2,4,5-tetraarylated imidazoles
    Behbahani, Farahnaz K.
    Yektanezhad, Talayeh
    MONATSHEFTE FUR CHEMIE, 2012, 143 (11): : 1529 - 1532
  • [44] One-Pot Synthesis of 2H-Thiochromenes via TiCl4-Promoted Reaction of 2-tert-Butylthiobenzaldehydes with Activated Alkenes
    Lee, Chang Hoon
    Lee, Kee-Jung
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (05) : 1023 - 1027
  • [45] One-pot synthesis of 1,2,4,5-tetra substituted imidazoles using sulfonic acid functionalized silica (SiO2-Pr-SO3H)
    Ziarani, Ghodsi Mohammadi
    Dashtianeh, Zeinab
    Nahad, Monireh Shakiba
    Badiei, Alireza
    ARABIAN JOURNAL OF CHEMISTRY, 2015, 8 (05) : 692 - 697
  • [46] One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with Hexamethyldisilazane in Molten Tetrabutylammonium Bromide
    Salehi, Javad
    Khodaei, Mohammad M.
    Khosropour, Ahmad R.
    SYNTHESIS-STUTTGART, 2011, (03): : 459 - 462
  • [47] Sodium bisulfite as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil or benzoin and aromatic aldehydes
    Sangshetti, Jaiprakash N.
    Kokare, Nagnnath D.
    Kotharkar, Sandeep A.
    Shinde, Devanand B.
    MONATSHEFTE FUR CHEMIE, 2008, 139 (02): : 125 - 127
  • [48] One-Pot, Simple and Efficient Synthesis of Triaryl-1H-imidazoles by KMnO4/CuSO4
    Khorramabadi-zad, Ahmad
    Azadmanesh, Mohammad
    Mohammadi, Somaye
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2013, 66 : 244 - 247
  • [49] SnCl4/SiO2: An Efficient Heterogeneous Alternative for One-pot Synthesis of β-Acetamidoketones
    Mirjalili, Bi Bi Fatemeh
    Hashemi, Mohammad M.
    Sadeghi, Bahareh
    Emtiazi, Hamideh
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2009, 56 (02) : 386 - 391
  • [50] ZrOCl2·8H2O catalyzed one-pot synthesis of 2,4,5-triaryl-1H-imidazoles and substituted 1,4-di(4,5-diphenylimidazolyl)benzene
    Jaiprakash N.Sangshetti
    Nagnnath D.Kokare
    Sandeep A.Kotharkar
    Devanand B.Shinde
    Chinese Chemical Letters, 2008, (07) : 762 - 766