Alumina Supported Ammonium Dihydrogenphosphate (NH4H2PO4/Al2O3): Preparation, Characterization and Its Application as Catalyst in the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles

被引:42
作者
Emrani, Anahita [1 ]
Davoodnia, Abolghasem [1 ]
Tavakoli-Hoseini, Niloofar [1 ]
机构
[1] Islamic Azad Univ, Mashhad Branch, Dept Chem, Mashhad, Iran
关键词
Alumina supported ammonium dihydrogenphosphate; Heterogeneous catalysis; Solvent-free conditions; Tetrasubstituted imidazoles; ONE-POT SYNTHESIS; REUSABLE HETEROGENEOUS CATALYST; SOLVENT-FREE CONDITIONS; ACIDIC IONIC LIQUID; SILICA-GEL; TETRASUBSTITUTED IMIDAZOLES; POLYPHOSPHORIC ACID; HIGHLY-EFFICIENT; FACILE SYNTHESIS; HCLO4-SIO2;
D O I
10.5012/bkcs.2011.32.7.2385
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Preparation of ammonium dihydrogenphosphate supported on alumina (NH4H2PO4/Al2O3) and its primary application as a solid acid supported heterogeneous catalyst to the synthesis of 1,2,4,5-tetrasubstituted imidazoles by a one-pot, four-component condensation of benzil, aromatic aldehydes, primary amines, and ammonium acetate under thermal solvent-free conditions were described. The results showed that the novel catalyst has high activity and the desired products were obtained in high yields. Furthermore, the products could be separated simply from the catalyst, and the catalyst could be recycled and reused with only slight reduction in its catalytic activity. Characterization of the catalyst was performed by FT-IR spectroscopy, the N-2 adsorption/desorption analysis (BET), thermal analysis (TG/DTG), and X-ray diffraction (XRD) techniques.
引用
收藏
页码:2385 / 2390
页数:6
相关论文
共 43 条
[1]   Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. [J].
Antolini, M ;
Bozzoli, A ;
Ghiron, C ;
Kennedy, G ;
Rossi, T ;
Ursini, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1023-1028
[2]   A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation [J].
Balalaie, S ;
Hashemi, MM ;
Akhbari, M .
TETRAHEDRON LETTERS, 2003, 44 (08) :1709-1711
[3]   SULPHUR-METHYLENE ISOSTERISM IN DEVELOPMENT OF METIAMIDE, A NEW HISTAMINE H2-RECEPTOR ANTAGONIST [J].
BLACK, JW ;
DURANT, GJ ;
EMMETT, JC ;
GANELLIN, CR .
NATURE, 1974, 248 (5443) :65-67
[4]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[5]   Reactivity of ionic liquids [J].
Chowdhury, Shahana ;
Mohan, Ram S. ;
Scott, Janet L. .
TETRAHEDRON, 2007, 63 (11) :2363-2389
[6]  
Clark J.H., 2000, RSC CLEAN TECHNOL MO
[7]   An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O [J].
Das Sharma, Salkat ;
Hazarika, Parasa ;
Konwar, Dilip .
TETRAHEDRON LETTERS, 2008, 49 (14) :2216-2220
[8]   A new route to the synthesis of thieno [2,3-d] pyrimidin-4(3H)-one derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40) [J].
Davoodnia, A. ;
Bakavoli, M. ;
Barakouhi, Gh. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1483-1486
[9]   A rapid synthesis of isoxazolo[5,4-d]pyrimidin-4(5H)-ones under microwave irradiation with solid acid catalysis in solvent-free conditions [J].
Davoodnia, A. ;
Roshani, M. ;
Malaeke, S. H. ;
Bakavoli, M. .
CHINESE CHEMICAL LETTERS, 2008, 19 (05) :525-528
[10]   Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst [J].
Davoodnia, A. ;
Allameh, S. ;
Fakhari, A. R. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2010, 21 (05) :550-553