Abstract
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.
Highlights
Pyridine moieties are common substructures in numerous natural products, pharmaceuticals, and functional materials.[1,2,3] Polysubstituted pyridines possess important biological and pharmacological activities and could be used as potential agrochemicals, for example as herbicides.[4]
Based on the above mentioned reports and in continuation of our efforts to develop facile and general methods for the preparation of 2-amino-3-cyanopyridine derivatives, and as a part of our studies to utilize heterogeneous catalyst for the synthesis of organic compounds,[27,28,29,30,31] here we wish to report a heterogeneous catalyst system based on Cu/C and illustrate its application for the synthesis of 2-amino3-cyanopyridine derivatives without any cocatalyst or activator under mild conditions
To exploit a method for the preparation of new 2-amino3-cyanopyridine derivatives, the reaction of acetophenone (1 mmol), benzaldehyde (1 mmol), malononitrile (1.5 mmol) and ammonium acetate (2 mmol) in the presence of Cu/C under air atmosphere was chosen as a model and its behavior was studied under a variety of conditions (Table 1)
Summary
Pyridine moieties are common substructures in numerous natural products, pharmaceuticals, and functional materials.[1,2,3] Polysubstituted pyridines possess important biological and pharmacological activities and could be used as potential agrochemicals, for example as herbicides.[4] In addition, the molecules containing pyridine moiety are used as non linear optical materials,[5] electrical materials,[6] and chelating agents in metal ligand chemistry.[7] Among them, 2-amino-3-cyanopyridines are known as IKK-β-inhibitors.[8] They have been identified to possess multiple biological activities such as antimicrobial,[9] antiviral,[10] antibacterial,[11] antifungal,[12] antitumor,[13] anti-inflammatory,[14] as well as antihypertensive[15] properties They are important and useful intermediates in preparing a variety of heterocyclic compounds.[12,16]. Based on the above mentioned reports and in continuation of our efforts to develop facile and general methods for the preparation of 2-amino-3-cyanopyridine derivatives, and as a part of our studies to utilize heterogeneous catalyst for the synthesis of organic compounds,[27,28,29,30,31] here we wish to report a heterogeneous catalyst system based on Cu/C and illustrate its application for the synthesis of 2-amino3-cyanopyridine derivatives without any cocatalyst or activator under mild conditions
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