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

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 36期

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

页码：4870 / 4872

页数：3

共 51 条

[1] One-step, three-component synthesis of highly substituted pyridines using silica nanoparticle as reusable catalyst [J].

Banerjee, Subhash ;

Sereda, Grigoriy .

TETRAHEDRON LETTERS, 2009, 50 (50) :6959-6962

[2] New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist n-ethylcarboxamidoadenosine [J].

Beukers, MW ;

Chang, LCW ;

Künzel, JKVD ;

Mulder-Krieger, T ;

Spanjersberg, RF ;

Brussee, J ;

Ijzerman, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (15) :3707-3709

[3] Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules [J].

Bhanushali, Mayur ;

Zhao, Cong-Gui .

SYNTHESIS-STUTTGART, 2011, (12) :1815-1830

[4] DIELS-ALDER REACTIONS OF N-SULFONYL-1-AZA-1,3-BUTADIENES - DEVELOPMENT OF A SYNTHETIC APPROACH TO THE STREPTONIGRONE C RING [J].

BOGER, DL ;

NAKAHARA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :880-884

[5] A GENERAL-SOLUTION TO IMPLEMENTING THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS - INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF ALPHA,BETA-UNSATURATED N-BENZENESULFONYL IMINES [J].

BOGER, DL ;

KASPER, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1517-1519

[6] A series of ligands displaying a remarkable agonistic-antagonistic profile at the adenosine A1 receptor [J].

Chang, LCW ;

Künzel, JKVF ;

Mulder-Krieger, T ;

Spanjersberg, RF ;

Roerink, SF ;

van den Hout, G ;

Beukers, MW ;

Brussee, J ;

IJzerman, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (06) :2045-2053

[7]

Chen H., 2005, WO, Patent No. [2005058315A1, 2005058315, 2005/058315]

[8] Synthesis and antiproliferative activity of 2,6-dibenzylamino-3,5-dicyanopyridines on human cancer cell lines [J].

Cocco, MT ;

Congiu, C ;

Lilliu, V ;

Onnis, V .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) :1365-1372

[9] Engineering Metal Organic Frameworks for Heterogeneous Catalysis [J].

Corma, A. ;

Garcia, H. ;

Llabres i Xamena, F. X. L. I. .

CHEMICAL REVIEWS, 2010, 110 (08) :4606-4655

[10] An Efficient Procedure for the Synthesis of Substituted Pyridines Using KF•Al2O3 [J].

Das, Biswanath ;

Ravikanth, Bommena ;

Kumar, Avula Satya ;

Kanth, Boddu Shashi .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) :1208-1212

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