Superparamagnetic Fe3O4@Alginate supported L-arginine as a powerful hybrid inorganic-organic nanocatalyst for the one-pot synthesis of pyrazole derivatives

被引:33
作者
Amirnejat, Sara [1 ]
Nosrati, Aliakbar [1 ]
Javanshir, Shahrzad [1 ]
机构
[1] Iran Univ Sci & Technol, Heterocycl Chem Res Lab, Dept Chem, Tehran 1684613114, Iran
关键词
inorganic-organic nanocatalyst; L-arginine; magnetic nanoparticles; pyrazoles; sodium alginate; HETEROGENEOUS CATALYST; BIOPOLYMERIC CATALYST; BIOLOGICAL EVALUATION; OXIDE NANOPARTICLES; GREEN SYNTHESIS; ALGINIC ACID; EFFICIENT; INHIBITORS; ADSORBENT; DESIGN;
D O I
10.1002/aoc.5888
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Hybrid inorganic-organic material Fe3O4@Alg@CPTMS@Arg, was prepared by the layer-by-layer techniques through grafting l-arginine (l-arg) to Fe3O4@Alg using 3-chloropropyltrimethoxysilane (CPTMS) as a linker. Fe3O4@Alg was prepared by in situ co-precipitation of iron (iii) and iron (ii) chloride in the presence alginate (Alg). The hybrid inorganic-organic material was characterized employing various techniques such as Fourier transform infrared (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), thermogravimetric analysis (TGA), and vibrating sample magnetometer (VSM). The as-prepared Fe3O4@Alg@CPTMS@Arg nanoparticles mediated the synthesis of pyrazole derivatives withviaone-pot reaction between phenylhydrazine, malononitrile, and various aromatic aldehydes under reflux in ethanol. Recycled catalyst exhibited comparable efficacy after seven cycles. The high catalytic activity, excellent yields, as well as the recyclability of the hybrid nanomaterials with quantitative efficiency, are factors that render this environmentally benign procedure appealing.
引用
收藏
页数:13
相关论文
共 51 条
[1]   Iron Oxide Nanoparticles: An Efficient Nano-catalyst [J].
Ahmad, Tokeer ;
Phul, Ruby ;
Khan, Huma .
CURRENT ORGANIC CHEMISTRY, 2019, 23 (09) :994-1004
[2]   A novel catalytic process for degradation of bisphenol A from aqueous solutions: A synergistic effect of nano-Fe3O4@Alg-Fe on O3/H2O2 [J].
Ahmadi, Mehdi ;
Rahmani, Hasan ;
Takdastan, Afshin ;
Jaafarzadeh, Neemat ;
Mostoufi, Azar .
PROCESS SAFETY AND ENVIRONMENTAL PROTECTION, 2016, 104 :413-421
[3]   Approaches in biotechnological applications of natural polymers [J].
Albuquerque, Priscilla B. S. ;
Coelho, Luana C. B. B. ;
Teixeira, Jose A. ;
Carneiro-da-Cunha, Maria G. .
AIMS MOLECULAR SCIENCE, 2016, 3 (03) :386-425
[4]   Cobalt ferrite encapsulated in a zwitterionic chitosan derived shell: An efficient nano-magnetic catalyst for three-component syntheses of pyrano[3,2-c]quinolines and spiro-oxindoles [J].
Asghari-Haji, Fatereh ;
Rad-Moghadam, Kurosh ;
Mahmoodi, Nosrat O. ;
Tonekaboni, Tayyebeh ;
Rahimi, Najmeh .
APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (12)
[5]   3,4-DIPHENYL-1H-PYRAZOLE-1-PROPANAMINE ANTIDEPRESSANTS [J].
BAILEY, DM ;
HANSEN, PE ;
HLAVAC, AG ;
BAIZMAN, ER ;
PEARL, J ;
DEFELICE, AF ;
FEIGENSON, ME .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (02) :256-260
[6]   Cinnamoyl nitrogen mustard derivatives of pyrazole analogues of tallimustine modified at the amidino moiety: design, synthesis, molecular modeling and antitumor activity studies [J].
Baraldi, PG ;
Beria, I ;
Cozzi, P ;
Geroni, C ;
Espinosa, A ;
Gallo, MA ;
Entrena, A ;
Bingham, JP ;
Hartley, JA ;
Romagnoli, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (14) :3911-3921
[7]   Design Polysaccharides of Marine Origin: Chemical Modifications to Reach Advanced Versatile Compounds [J].
Chopin, Nathalie ;
Guillory, Xavier ;
Weiss, Pierre ;
Le Bideau, Jean ;
Colliec-Jouault, Sylvia .
CURRENT ORGANIC CHEMISTRY, 2014, 18 (07) :867-895
[8]   Alginic acid: A mild and renewable bifunctional heterogeneous biopolymeric organocatalyst for efficient and facile synthesis of polyhydroquinolines [J].
Dekamin, Mohammad G. ;
Karimi, Zahra ;
Latifidoost, Zahra ;
Ilkhanizadeh, Siamand ;
Daemi, Hamed ;
Naimi-Jamal, M. Reza ;
Barikani, Mehdi .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2018, 108 :1273-1280
[9]   Sodium alginate: An efficient biopolymeric catalyst for green synthesis of 2-amino-4H-pyran derivatives [J].
Dekamin, Mohammad G. ;
Peyman, S. Zahra ;
Karimi, Zahra ;
Javanshir, Shahrzad ;
Naimi-Jamal, M. Reza ;
Barikani, Mehdi .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2016, 87 :172-179
[10]   Alginic acid: a highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines [J].
Dekamin, Mohammad G. ;
Ilkhanizadeh, Siamand ;
Latifidoost, Zahra ;
Daemi, Hamed ;
Karimi, Zahra ;
Barikani, Mehdi .
RSC ADVANCES, 2014, 4 (100) :56658-56664