Calcium, Barium and Strontium apatites: A new generation of catalysts in the Biginelli reaction

被引:20
作者
Ben Moussa, Sana [1 ]
Lachheb, Jalel [1 ]
Gruselle, Michel [2 ,3 ]
Maaten, Birgit [4 ]
Kriis, Kadri [5 ]
Kanger, Tonis [5 ]
Tonsuaadu, Kaia [6 ]
Badraoui, Bechir [1 ]
机构
[1] Univ Monastir, Inst Preparatoire Etud Ingenieurs Monastir, UR Mat & Synth Organ UR 17E531, Monastir 5019, Tunisia
[2] CNRS, UMR 8232, Inst Parisien Chim Mol, F-75005 Paris, France
[3] UPMC Univ Paris 06, Sorbonne Univ, Inst Parisien Chim Mol, UMR 8232, F-75005 Paris, France
[4] Tallinn Univ Technol, Dept Energy Technol, Ehitajate Tee 5, EE-19086 Tallinn, Estonia
[5] Tallinn Univ Technol, Dept Chem & Biotechnol, Akad Tee 15, EE-12618 Tallinn, Estonia
[6] Tallinn Univ Technol, Lab Inorgan Mat, Ehitajate Tee 5, EE-19086 Tallinn, Estonia
关键词
Biginelli reaction; Hydroxyapatite; Modified hydroxyapatite; Catalysis; SOLVENT-FREE CONDITIONS; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYSTS; ASSISTED SYNTHESIS; MOLECULAR-OXYGEN; HYDROXYAPATITE; EFFICIENT; ACID; FLUORAPATITE; OXIDATION;
D O I
10.1016/j.tet.2017.09.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe herein the use of Calcium, Barium and Strontium hydroxyapatites (CaHAp, BaHAp and SrHAp) as well as CaHAp containing Magnesium, Copper, Zinc and Palladium (MgHAp, CuHAp, ZnHAp and PdHAp) as catalysts in the Biginelli reaction. The efficiency of CaHAp and SrHAp is very low, leading to the expected 3,4-dihydropyrimidin-2(1H)-one in poor yields. Mixed Ba(5)Sr(5)HAp and BaioHAp show interesting catalytic properties, especially BaioHAp leading to pure isolated reaction products in good yields. The use of modified CaHAp seems to be of interest in regard to the yield obtained. Nevertheless the release of Mg, Cu, Zn and Pd ions in the solution during the catalytic process makes the use of such modified apatites less effective. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6542 / 6548
页数:7
相关论文
共 56 条
[1]   Dihydropyrimidones: As novel class of β-glucuronidase inhibitors [J].
Ali, Farman ;
Khan, Khalid Mohammed ;
Salar, Uzma ;
Iqbal, Sarosh ;
Taha, Muhammad ;
Ismail, Nor Hadiani ;
Perveen, Shahnaz ;
Wadood, Abdul ;
Ghufran, Mehreen ;
Ali, Basharat .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (16) :3624-3635
[2]   An Efficient Biginelli One-Pot Synthesis of New Benzoxazole-Substituted Dihydropyrimidinones and Thiones Catalysed by Alumina-Supported Trifluoromethane Sulfonic Acid Under Solvent Free Conditions [J].
Arjun, M. ;
Sridhar, D. ;
Chari, M. Adharvana ;
Sarangapani, M. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (01) :119-123
[3]   An efficient one-pot synthesis of dihydropyrimidinones catalyzed by zirconium hydrogen phosphate under solvent-free conditions [J].
Besoluk, Senol ;
Kucukislamoglu, Mustafa ;
Zengin, Mustafa ;
Arslan, Mustafa ;
Nebioglu, Mehmet .
TURKISH JOURNAL OF CHEMISTRY, 2010, 34 (03) :411-416
[4]   MAGNESIUM INFLUENCE ON HYDROXYAPATITE CRYSTALLIZATION [J].
BIGI, A ;
FALINI, G ;
FORESTI, E ;
GAZZANO, M ;
RIPAMONTI, A ;
ROVERI, N .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1993, 49 (01) :69-78
[5]  
Biginelli P., 1891, Berichte Der Deutschen Chemischen Gesellschaft, V24, P2962, DOI 10.1002/cber.189102402126
[6]  
Biginelli P., 1891, BERICHTE DTSCH CHEM, V24, P1317, DOI 10.1002/cber.189102401228
[7]   Hydroxyapatite nanocrystals modified with acidic amino acids [J].
Boanini, Elisa ;
Fini, Milena ;
Gazzano, Massimo ;
Bigi, Adriana .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (23) :4821-4826
[8]   Recyclable CuS quantum dots as heterogeneous catalyst for Biginelli reaction under solvent free conditions [J].
Chaudhary, Ganga Ram ;
Bansal, Pratibha ;
Mehta, S. K. .
CHEMICAL ENGINEERING JOURNAL, 2014, 243 :217-224
[9]   The Combined Role of Catalysis and Solvent Effects on the Biginelli Reaction: Improving Efficiency and Sustainability [J].
Clark, James H. ;
Macquarrie, Duncan J. ;
Sherwood, James .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (16) :5174-5182
[10]   Synthesis of 3,4-dihydropyrimidin-2-ones catalysed by fluorapatite doped with metal halides [J].
El Badaoui, H ;
Bazi, F ;
Tahir, R ;
Lazrek, HB ;
Sebti, S .
CATALYSIS COMMUNICATIONS, 2005, 6 (07) :455-458