A series of phenyl sulfonate metal coordination polymers as catalysts for one-pot Biginelli reactions under solvent-free conditions

被引:32
作者
Wang, Jin-Hua [1 ]
Tang, Gui-Mei [1 ]
Wang, Yong-Tao [1 ]
Cui, Yue-Zhi [1 ]
Wang, Jun-Jie [2 ]
Ng, Seik Weng [3 ]
机构
[1] Qilu Univ Technol, Dept Chem Engn, Shandong Prov Key Lab Fine Chem, Jinan 250353, Peoples R China
[2] Anyang Normal Univ, Dept Chem, Anyang 455002, Henan, Peoples R China
[3] Univ Malaya, Dept Chem, Kuala Lumpur 50603, Malaysia
关键词
CALCIUM-CHANNEL BLOCKERS; ORGANIC FRAMEWORK; HETEROGENEOUS CATALYST; HIGHLY EFFICIENT; CRYSTAL-STRUCTURE; IONIC LIQUIDS; ACID-ESTERS; CO2; CAPTURE; GREEN; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES;
D O I
10.1039/c5dt03135d
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Three new metal coordination polymers, namely, [Co(DPP)(2)(H2O)(2)]center dot(BS)(2)center dot 2H(2)O (1), [Co(DPP)(2)(H2O)(2)]center dot(ABS)(2)center dot 2H(2)O (2) and [Co(DPP)(2)(MBS)(2)] (3) [DPP = 1,3-di(pyridin-4-yl) propane, BS = phenyl sulfonic acid, ABS = p-aminobenzene sulfonic acid, MBS = p-methylbenzene sulfonic acid] were obtained under hydrothermal conditions. Complexes 1-3 were structurally characterized using X-ray single-crystal diffraction, XRD and IR spectroscopy. Both complexes 1 and 2 display a 1D tape structure. Meanwhile, complex 3 exhibits a 2D layer and further stacks via C-H center dot center dot center dot pi interactions to generate a three-dimensional supramolecular architecture. These three metal coordination polymers have been applied as catalysts for the green synthesis of a variety of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions through the Biginelli reaction. Interestingly, the catalysis products have been obtained in high yields under eco-friendly synthesis conditions.
引用
收藏
页码:17829 / 17840
页数:12
相关论文
共 110 条
[1]  
Alessandro D., 2001, TETRAHEDRON LETT, V42, P7975, DOI DOI 10.1016/S0040-4039(01)01728-2
[2]  
[Anonymous], 1996, SADABS
[3]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
KIMBALL, SD ;
FLOYD, DM ;
MORELAND, S ;
SWANSON, BN ;
GOUGOUTAS, JZ ;
SCHWARTZ, J ;
SMILLIE, KM ;
MALLEY, MF .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635
[4]   Luminescent Cyclometalated Alkynylgold(III) Complexes with 6-Phenyl-2,2′-Bipyridine Derivatives: Synthesis, Characterization, Electrochemistry, Photophysics, and Computational Studies [J].
Au, Vonika Ka-Man ;
Lam, Wai Han ;
Wong, Wing-Tak ;
Yam, Vivian Wing-Wah .
INORGANIC CHEMISTRY, 2012, 51 (14) :7537-7545
[5]   Highly luminescent terpyridinyl-ethynyl functionalized dithieno[3,2-b:2′,3′-d]phospholes: synthesis, properties and complexation behavior [J].
Bai, Dong Ren ;
Romero-Nieto, Carlos ;
Baumgartner, Thomas .
DALTON TRANSACTIONS, 2010, 39 (05) :1250-1260
[6]   Ligand field effect tuned magnetic behaviors of two chain compounds based on Mn3IIIO units: from slow magnetic relaxation to metamagnetism [J].
Bai, Yue-Ling ;
Bao, Xiaoli ;
Zhu, Shourong ;
Fang, Jianhui ;
Tao, Jun .
DALTON TRANSACTIONS, 2013, 42 (04) :1033-1038
[7]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[8]  
Biginelli P., 1891, BERICHTE DTSCH CHEM, V24, P1317, DOI 10.1002/cber.189102401228
[9]   Luminescent Triarylboron-Functionalized Zinc Carboxylate Metal-Organic Framework [J].
Blight, Barry A. ;
Guillet-Nicolas, Remy ;
Kleitz, Freddy ;
Wang, Rui-Yao ;
Wang, Suning .
INORGANIC CHEMISTRY, 2013, 52 (04) :1673-1675
[10]  
Bruker AXS, 1998, SAINT SOFTWARE REFER