Multi-component synthesis of 2-amino-6-(alkylthio)pyridine-3,5-dicarbonitriles using Zn(II) and Cd(II) metal-organic frameworks (MOFs) under solvent-free conditions

被引:46
作者
Thimmaiah, Muralidhara [1 ]
Li, Peng [1 ]
Regati, Sridhar [1 ]
Chen, Banglin [1 ]
Zhao, John Cong-Gui [1 ]
机构
[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA
基金
美国国家卫生研究院;
关键词
Metal-organic frameworks; Multi-component reaction; Heterogeneous catalysis; Benzaldehyde; Pyridine; HIGHLY SUBSTITUTED PYRIDINES; DIELS-ALDER REACTIONS; ONE-POT; 3-COMPONENT SYNTHESIS; IONIC LIQUID; ENANTIOSELECTIVE SYNTHESIS; PRION DISEASE; ONE-STEP; ADENOSINE; CATALYSTS;
D O I
10.1016/j.tetlet.2012.06.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Multi-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines has been developed by using the reaction of aldehydes, malononitrile, and thiophenols in the presence of a Zn(II) or a Cd(II) metal-organic framework (MOF) as the heterogeneous catalyst. This protocol tolerates different functional groups on the substrates and does not require the use of any organic solvent. Moreover, the Zn(II) and Cd(II) MOF catalysts can be recovered and reused for a number of runs without loss of activity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4870 / 4872
页数:3
相关论文
共 51 条
[11]  
Davoodnia A, 2011, ASIAN J CHEM, V23, P1273
[12]   Primary Amine Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones [J].
Ding, Derong ;
Zhao, Cong-Gui .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (20) :3802-3805
[13]   One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols [J].
Evdokimov, Nikolai M. ;
Kireev, Artem S. ;
Yakovenko, Andrey A. ;
Antipin, Mikhail Yu. ;
Magedov, Igor V. ;
Kornienko, Alexander .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3443-3453
[14]   One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility [J].
Evdokimov, NM ;
Magedov, IV ;
Kireev, AS ;
Kornienko, A .
ORGANIC LETTERS, 2006, 8 (05) :899-902
[15]  
Fredholm BB, 2001, PHARMACOL REV, V53, P527
[16]   Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles [J].
Gogoi, Sanjib ;
Zhao, Cong-Gui .
TETRAHEDRON LETTERS, 2009, 50 (19) :2252-2255
[17]   Synthesis and evaluation of a focused library of pyridine dicarbonitriles against prion disease [J].
Guo, Kai ;
Mutter, Roger ;
Heal, William ;
Reddy, Tummala R. K. ;
Cope, Hannah ;
Pratt, Steven ;
Thompson, Mark J. ;
Chen, Beining .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (01) :93-106
[18]   Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries [J].
Guo, Kai ;
Thompson, Mark J. ;
Reddy, Tummala R. K. ;
Mutter, Roger ;
Chen, Beining .
TETRAHEDRON, 2007, 63 (24) :5300-5311
[19]   Exploring Catalyst and Solvent Effects in the Multicomponent Synthesis of Pyridine-3,5-dicarbonitriles [J].
Guo, Kai ;
Thompson, Mark J. ;
Chen, Beining .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) :6999-7006
[20]  
Harada H., 2002, Int PCT., WO Patent, Patent No. [2002006237Al, 2002006237, WO 2002006237]