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:70
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
[61]  
Schmierer R., 1987, German Patent, Patent No. 361464
[62]  
Shrinivasa R., 2003, BIOORGAN MED CHEM, V13, P657
[63]  
Siddiqui N, 2008, ACTA POL PHARM, V65, P449
[64]   Synthesis and characterization of NiFe2O4 nanoparticles and nanorods [J].
Sivakumar, P. ;
Ramesh, R. ;
Ramanand, A. ;
Ponnusamy, S. ;
Muthamizhchelvan, C. .
JOURNAL OF ALLOYS AND COMPOUNDS, 2013, 563 :6-11
[65]   Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases [J].
Sondhi, Sham M. ;
Singh, Nirupma ;
Kumar, Ashok ;
Lozach, Olivier ;
Meijer, Laurent .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (11) :3758-3765
[66]  
Stella P.C.R., 2012, J CHEM PHARM RES, V4, P2988
[67]  
Stephen MC, 1987, BIOCHEM PHARMACOL, V36, P673, DOI [10.1016/0006-2952(87)90718-0, DOI 10.1016/0006-2952(87)90718-0]
[68]   The first principle computational study for the competitive mechanisms of oxidative aromatization of 2-substituted imidazolines using KMnO4/SiO2 [J].
Taherpour, Avat Arman ;
Yari, Ako ;
Ghasemhezaveh, Fatemeh ;
Zolfigol, Mohammad Ali .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (12) :2485-2493
[69]   The identification of potent and selective imidazole-based inhibitors of B-Raf kinase [J].
Takle, AK ;
Brown, MJB ;
Davies, S ;
Dean, DK ;
Francis, G ;
Gaiba, A ;
Hird, AW ;
King, FD ;
Lovell, PJ ;
Naylor, A ;
Reith, AD ;
Steadman, JG ;
Wilson, DM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (02) :378-381
[70]   CYP2C19 genotype-related efficacy of omeprazole for the treatment of infection caused by Helicobacter pylori [J].
Tanigawara, Y ;
Aoyama, N ;
Kita, T ;
Shirakawa, K ;
Komada, F ;
Kasuga, M ;
Okumura, K .
CLINICAL PHARMACOLOGY & THERAPEUTICS, 1999, 66 (05) :528-534