A Multicomponent Synthesis of 2-Amino-3-cyanopyridine Derivatives Catalyzed by Heterogeneous and Recyclable Copper Nanoparticles on Charcoal

被引:52
作者
Khalifeh, Reza [1 ]
Ghamari, Mahdiyeh [1 ]
机构
[1] Shiraz Univ Technol, Dept Chem, Shiraz 71555313, Iran
关键词
2-amino-3-cyanopyridine; Cu/C; heterogeneous catalyst; multicomponent reaction; MANNICH REACTION; GREEN SOLVENT; LARIAT ETHERS; IN-VITRO; EFFICIENT; AGENTS; INHIBITORS; GRAPHITE; ANALOGS; ALKYNES;
D O I
10.5935/0103-5053.20150327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and convenient method was developed for synthesis of 2-amino-3-cyanopyridine derivatives via the four-component coupling reaction between ketone, aldehyde, malononitrile, and ammonium acetate in the presence of 2 mol% copper nanoparticles on charcoal (Cu/C) catalyst. A variety of ketones and aldehydes was used to afford the corresponding products in good to excellent yields. The method is applicable to large-scale operation without any problem. The catalyst could be quantitatively recovered from the reaction mixture by simple filtration and reused at least eight times with almost consistent activity.
引用
收藏
页码:759 / 768
页数:10
相关论文
共 31 条
[1]   HETEROCYCLIC-ANALOGS OF THE ANTIHYPERTENSIVE BETA-ADRENERGIC BLOCKING-AGENT (S)-2-[3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY]-3-CYANOPYRIDINE [J].
BALDWIN, JJ ;
ENGELHARDT, EL ;
HIRSCHMANN, R ;
PONTICELLO, GS ;
ATKINSON, JG ;
WASSON, BK ;
SWEET, CS ;
SCRIABINE, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (01) :65-70
[2]   Synthesis of aminonicotinonitriles and diaminopyridines through base-catalyzed ring transformation of 2H-pyran-2-ones [J].
Farhanullah ;
Agarwal, N ;
Goel, A ;
Ram, VJ .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2983-2985
[3]   Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues [J].
Gholap, Atul R. ;
Toti, Kiran S. ;
Shirazi, Fazal ;
Kumari, Ratna ;
Bhat, Manoj Kumar ;
Deshpande, Mukund V. ;
Srinivasan, Kumar V. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) :6705-6715
[4]  
Hammam AEG, 2000, Z NATURFORSCH B, V55, P417
[5]   De novo synthesis of substituted pyridines [J].
Henry, GD .
TETRAHEDRON, 2004, 60 (29) :6043-6061
[6]  
JONES G, 1996, COMPREHENSIVE HETERO, V5
[7]   PREPARATION AND PROPERTIES OF HIGHLY ELECTRON-ACCEPTING POLY(PYRIMIDINE-2,5-DIYL) [J].
KANBARA, T ;
KUSHIDA, T ;
SAITO, N ;
KUWAJIMA, I ;
KUBOTA, K ;
YAMAMOTO, T .
CHEMISTRY LETTERS, 1992, (04) :583-586
[8]   Synthesis of [Zn()BHPPDAH] as New Heterogeneous Catalyst without Being Immobilized on Any Support and Applied for Mannich Reaction [J].
Khalifeh, Reza ;
Sharghi, Hashem ;
Rashidi, Zahra .
HETEROATOM CHEMISTRY, 2013, 24 (05) :372-383
[9]  
Konda S., 2010, J. Chem. Pharm. Res, V2, P187
[10]   Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: Parallel synthesis, bioactivity, and in vitro pharmacokinetics [J].
May, Barnaby C. H. ;
Zorn, Julie A. ;
Witkop, Juanita ;
Sherrill, John ;
Wallace, Andrew C. ;
Legname, Giuseppe ;
Prusiner, Stanley B. ;
Cohen, Fred E. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (01) :65-73