Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5-trisubstituted imidazoles, benzo[d]imidazoles, benzo[d]oxazoles and azo-linked benzo[d]oxazoles

被引:67
作者
Fekri, Leila Zare [1 ]
Nikpassand, Mohammad [2 ]
Shariati, Shahab [2 ]
Aghazadeh, Behnaz [2 ]
Zarkeshvari, Reza [1 ]
Pour, Nahid Norouz [1 ]
机构
[1] Payame Noor Univ, Dept Chem, POB 19395-3697, Tehran, Iran
[2] Islamic Azad Univ, Rasht Branch, Dept Chem, Rasht, Iran
关键词
Oxazoles; Imidazoles; NiFe2O4@SiO2@amino glucose; Solvent free reaction; ONE-POT SYNTHESIS; PHENOLIC SCHIFFS BASES; TETRASUBSTITUTED IMIDAZOLES; OXIDATIVE CYCLIZATION; BIOLOGICAL-PROPERTIES; EFFICIENT SYNTHESIS; AMMONIUM ACETATE; DERIVATIVES; BENZOXAZOLE; 2,4,5-TRIARYL-1H-IMIDAZOLES;
D O I
10.1016/j.jorganchem.2018.07.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chemically synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform infrared spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzofdlimidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their physical constant, comparison with authentic samples, FT-IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2018 Elsevier B.V. All rights reserved.
引用
收藏
页码:60 / 73
页数:14
相关论文
共 83 条
  • [1] Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)
    Aiello, Stefania
    Wells, Geoffrey
    Stone, Erica L.
    Kadri, Hachemi
    Bazzi, Rana
    Bell, David R.
    Stevens, Malcolm F. G.
    Matthews, Charles S.
    Bradshaw, Tracey D.
    Westwell, Andrew D.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) : 5135 - 5139
  • [2] Albert D, 2009, BIOORG MED CHEM LETT, V19, P5962, DOI [10.1016/j.bmcl.2009.08.013, DOI 10.1016/J.BMCL.2009.08.013]
  • [3] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .39. SYNTHESIS OF BENZIMIDAZOLES CONTAINING A FUSED ALICYCLIC RING BY RHODIUM - CATALYZED HYDROFORMYLATION OF N-ALKENYL-1,2-DIAMINOBENZENES
    ANASTASIOU, D
    CAMPI, EM
    CHAOUK, H
    JACKSON, WR
    [J]. TETRAHEDRON, 1992, 48 (36) : 7467 - 7478
  • [4] Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents.
    Antolini, M
    Bozzoli, A
    Ghiron, C
    Kennedy, G
    Rossi, T
    Ursini, A
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) : 1023 - 1028
  • [5] Arakawa K, 1997, CHEM PHARM BULL, V45, P1984
  • [6] Acetic acid-promoted condensation of o-phenylenediamine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles under microwave irradiation
    Azarifar, Davood
    Pirhayati, Mojgan
    Maleki, Behrooz
    Sanginabadi, Mehrangiz
    Yami, Razieh Nejat
    [J]. JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2010, 75 (09) : 1181 - 1189
  • [7] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Nejati, Akbar
    [J]. GREEN CHEMISTRY, 2010, 12 (07) : 1237 - 1241
  • [8] A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation
    Balalaie, S
    Hashemi, MM
    Akhbari, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (08) : 1709 - 1711
  • [9] One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation
    Balalaie, S
    Arabanian, A
    [J]. GREEN CHEMISTRY, 2000, 2 (06) : 274 - 276
  • [10] An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles
    Brain, CT
    Brunton, SA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (10) : 1893 - 1895