Preparation and characterization of Fe3O4@SiO2/APTPOSS core-shell composite nanomagnetics as a novel family of reusable catalysts and their application in the one-pot synthesis of 1,3-thiazolidin-4-one derivatives

被引:22
作者
Safaei-Ghomi, Javad [1 ]
Nazemzadeh, Seyed Hadi [1 ]
Shahbazi-Alavi, Hossein [1 ]
机构
[1] Univ Kashan, Fac Chem, Dept Organ Chem, Kashan 87317, Iran
关键词
Fe3O4; MNPs; 1,3-thiazolidin-4-one; solvent-free; POSS; POLYHEDRAL OLIGOMERIC SILSESQUIOXANES; ANTI-HIV AGENTS; HETEROGENEOUS CATALYST; ANTIMICROBIAL ACTIVITY; FE3O4; NANOPARTICLES; SILICA; POSS; 2,3-DIARYL-1,3-THIAZOLIDIN-4-ONES; EFFICIENT; DESIGN;
D O I
10.1002/aoc.3520
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Octakis[3-(3-aminopropyltriethoxysilane)propyl]octasilsesquioxane (APTPOSS) as a polyhedral oligomeric silsesquioxane derivative was prepared and used as a pioneer reagent to obtain a novel core-shell composite using magnetic iron oxide nanoparticles as the core and the inorganic-organic hybrid polyhedral oligomeric silsesquioxane as the shell. Fe3O4@SiO2/APTPOSS were confirmed using Fourier transform infrared spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, dynamic light scattering, thermogravimetric analysis, X-ray diffraction and vibrating sample magnetometry. The inorganic-organic hybrid polyhedral oligomeric silsesquioxane magnetic nanoparticles were used as an efficient new heterogeneous catalyst for the onepot three-component synthesis of 1,3-thiazolidin-4-ones under solvent-free conditions. Moreover, these nanoparticles could be easily separated using an external magnet and then reused several times without significant loss of catalytic activity. Copyright (C) 2016 John Wiley & Sons, Ltd.
引用
收藏
页码:911 / 916
页数:6
相关论文
共 37 条
[1]   Magnetically retrievable catalysts for organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL COMMUNICATIONS, 2013, 49 (08) :752-770
[2]   SILSESQUIOXANES [J].
BANEY, RH ;
ITOH, M ;
SAKAKIBARA, A ;
SUZUKI, T .
CHEMICAL REVIEWS, 1995, 95 (05) :1409-1430
[3]   Design, synthesis, structure-activity relationships, and molecular modeling studies of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents [J].
Barreca, ML ;
Balzarini, J ;
Chimirri, A ;
De Clercq, E ;
De Luca, L ;
Höltje, HD ;
Höltje, M ;
Monforte, AM ;
Monforte, P ;
Pannecouque, C ;
Rao, A ;
Zappalà, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (24) :5410-5413
[4]   Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents [J].
Barreca, ML ;
Chimirri, A ;
De Luca, L ;
Monforte, AM ;
Monforte, P ;
Rao, A ;
Zappalà, M ;
Balzarini, J ;
De Clercq, E ;
Pannecouque, C ;
Witvrouw, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1793-1796
[5]   Recent Developments in the Chemistry of Cubic Polyhedral Oligosilsesquioxanes [J].
Cordes, David B. ;
Lickiss, Paul D. ;
Rataboul, Franck .
CHEMICAL REVIEWS, 2010, 110 (04) :2081-2173
[6]   Nano magnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica hybrid: Synthesis, characterization, and application as an efficient and reusable organic-inorganic hybrid silica with ionic liquid framework for one-pot synthesis of pyran annulated heterocyclic compounds in water [J].
Davarpanah, Jamal ;
Kiasat, Ali Reza ;
Noorizadeh, Siamak ;
Ghahremani, Mahboubeh .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 376 :78-89
[7]   FUNCTIONALIZED OCTA-(PROPYLSILSESQUIOXANES) (3-XC(3)H(6))(8)(SI8O12) - MODEL COMPOUNDS FOR SURFACE-MODIFIED SILICA-GELS [J].
DITTMAR, U ;
HENDAN, BJ ;
FLORKE, U ;
MARSMANN, HC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 489 (1-2) :185-194
[8]   Synthesis and structure-activity relationships of 2-(substituted phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones acting as H1-histamine antagonists [J].
Diurno, MV ;
Mazzoni, O ;
Correale, G ;
Monterrey, IG ;
Calignano, A ;
La Rana, G ;
Bolognese, A .
FARMACO, 1999, 54 (09) :579-583
[9]   One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH2COOH)3 as catalyst [J].
Foroughifar, Naser ;
Ebrahimi, Sattar .
CHINESE CHEMICAL LETTERS, 2013, 24 (05) :389-391
[10]   Nano-magnetite (Fe3O4) as a support for recyclable catalysts in the development of sustainable methodologies [J].
Gawande, Manoj B. ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (08) :3371-3393