79388-04-8

Usage

Uses

Used in Pharmaceutical Industry:
1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile is used as a key intermediate in the synthesis of pharmaceutical drugs for its potential to contribute to the development of new medications.
Used in Organic Chemistry Research:
In the field of organic chemistry, 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile serves as a valuable component in the exploration of new materials and reactions, furthering scientific understanding and innovation.
Used in Material Science:
1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile is also utilized in material science for the development of new materials, capitalizing on its unique structural attributes and functional groups to create novel substances with potential applications in various industries.

Upstream product

• 140-87-4 Cyanoacetohydrazide 
• 2700-22-3 Benzylidenemalononitrile 
• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 109-77-3 malononitrile 
• 4974-44-1 N'-benzylidenecyanoacetohydrazide 

Downstream Products

• 1038081-85-4 1-amino-6-(triphenylphosphoranylideneamino)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrileiminophosphorane 
• 1316852-74-0 (Z)-methyl 4-((9-cyano-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridin-2-ylidene)methyl)benzoate 
• 1316852-73-9 (Z)-2-(4-bromobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-72-8 (Z)-2-(4-dimethylaminobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-71-7 (Z)-7-isocyano-2-(4-methoxybenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-70-6 (Z)-2-(4-nitrobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-69-3 (Z)-2-(4-chlorobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-68-2 (Z)-2-benzylidene-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-77-3 (Z)-2-(4-(tert-butyl)benzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-76-2 (Z)-7-isocyano-2-(4-isopropylbenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-75-1 (Z)-7-isocyano-2-(4-methylbenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1038081-88-7 5-oxo-7-phenyl-2-thiol-3,5-dihydro[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbonitrile 
• 67720-42-7 6-amino-1,2-dihydro-2-oxo-4-phenylpyridine-3,5-dicarbonitrile 
• 124443-23-8 2-methyl-5-oxo-7-phenyl-3,5-dihydro-<1,2,4>triazolo<1,5-a>pyridine-6,8-dicarbonitrile 

Relevant academic research and scientific papers

A comparative screening of the catalytic activity of nanocrystalline MIIZr4(PO4)6 ceramics in the one-pot synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile derivatives

A four-component reaction of hydrazine hydrate, ethyl cyanoacetate, malononitrile, and aromatic aldehydes was achieved in the presence of nanocrystalline MIIZr4(PO4)6 ceramics (MII: Mn, Fe, Co, Ni, Cu, Zn, Cd) as heterogeneous catalysts to produce N-amino-2-pyridones. The reactions were performed in the presence of different catalysts, and it is observed that CdZr4(PO4)6 nanocrystallines are the best catalysts among those examined. Atom economy, excellent yields in short times, high catalytic activity, recycling of catalyst, and environmental benignity are some of the important features of this protocol.

Pyrido triazin-nucleus synthesis and theoretical studies: 2,3,6-trioxo-8-aryl-1,3,4,6-tetrahydro-]2H[pyrido]1,2-b] [1,2,4[triazin-7,9-dicarbonitryl derivatives

An efficient method for the synthesis of potentially biologically [2H]-pyrido [1,2-b]1,2,4-triazines derivatives is described via reaction of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile derivatives with oxalyl chloride in DMF in the presence of pyridine as a base. The intramolecular hydrogen bonding (IMHB) interactions have been investigated at M06-2X/6-311++G(d,p) level of theory. The eight compounds (5a-h) characterized by geometries and energies. The Natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) were performed to explore the nature of the hydrogen-bonding interactions in these compounds. The IMHB formed between the C[dbnd]O and N[sbnd]H groups. The theoretical calculations showed that the IMHB strength increases in the presence of electron-donor substituents. An opposite behavior was observed for electron-acceptor substituents.

An efficient method for the synthesis of N-amino-2-pyridones using reusable catalyst ZnO nanoparticles

A concise and highly efficient protocol for the synthesis of N.amino-2-pyridones has been developed by a four-component coupling of hydrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes in the presence of ZnO nanoparticles under mild conditions. The key advantages of this process are using an inexpensive and reusable catalyst, easy work.up and excellent yields.

1,6-Diamino-2-oxopyridine-3,5-dicarbonitrile Derivatives in the Mannich Reaction

Abstract: 1,6-Diamino-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarbonitriles under the action of primary aliphatic amines and an excess of 37% formalin in ethanol were converted into 2,3,8,9-tetrahydro-6,10-methano[1,2,4]triazolo[1,5-a][1,5]diazocine-6,10(7

Triazole-Pyridine Dicarbonitrile Targets Phosphodiesterase 4 to Induce Cytotoxicity in Lung Carcinoma Cells

Phosphodiesterase 4 (PDE4) is a key enzyme involved in the hydrolysis of cyclic adenosine monophosphate (cAMP) and widely expressed in several types of cancers. The inhibition of PDE4 results in an increased concentration of intracellular cAMP levels that imparts the anti-inflammatory response in the target cells. In the present report, two series of triazolo-pyridine dicarbonitriles and substituted dihydropyridine dicarbonitriles were synthesized using green protocol (TBAB in refluxed water). We next evaluated the title compounds for their cytotoxicity towards lung cancer (A549) cells and identified 7′-[4-(methylsulfonyl)phenyl]-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5h) and 7′-(1-methyl-1H-imidazol-2-yl)-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5j) as lead analogs with the IC50 values of 15.2 and 24.1 μm, respectively. Furthermore, all the new compounds were tested for PDE4 inhibitory activity and 5j showed relatively good inhibitory activity towards PDE4 with inhibition of 50.9 % at 10 μm. In silico analysis demonstrated the favorable interaction of the title compounds with the target enzyme. Taken together, the present study introduces a new scaffold for the development of novel PDE4 inhibitors to fight against inflammatory diseases.

Convenient Synthesis of New Boric Acid Catalyzed 1,2,4-Triazolopyridinone Derivatives and an Investigation of their Optical Properties

Syntheses of fused heterobicyclic systems containing 1,2,4-triazolopyridinone moieties were accomplished by heterocyclization of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles and ninhydrin in ethanol and in the presence of boric acid as a catalyst in 30?min at room temperature. All compounds have been screened for their photophysical properties. Results showed that all compounds exhibit near infrared emissions at 876?nm.

Dipyrido[1,2-b:3′,4′-e][1,2,4]triazine Scaffolds from Pentafluoropyridine

Annelation reaction between pentafluoropyridine and diaminodihydro substituted pyridine derivatives gave dipyrido[1,2-b:3′,4′-e][1,2,4]triazine systems as major products arising from the initial nucleophilic substitution of more nucleophilic N-amino group

An efficient and ecofriendly synthesis of highly functionalized pyridones: Via a one-pot three-component reaction

A simple and convenient protocol has been developed for the synthesis of N-amino-3-cyano-2-pyridone derivatives by a one-pot reaction of cyanoacetohydrazide, activated nitrile substrates (malononitrile, ethyl cyanoacetate, cyanoacetamide) and aromatic ald

A three component one-pot synthesis of N-amino-2-pyridone derivatives catalyzed by KF-Al2O3

Synthesis of 1,6-diamino-4-phenyl-3,5-dicyano-2-pyridone derivatives via a one-pot, three-component reaction of aryl aldehydes, malononitrile, and cyanoacetic hydrazide at room temperature using KF-Al2O3 as a recyclable catalyst have been developed. The reaction proceeds through the initial Knoevenagel condensation between aldehyde and malononitrile in the presence of KF-Al2O3 to form the benzylidene derivative which then undergoes Michael addition with cyanoacetic hydrazide followed by intramolecular cyclization of the resulting intermediate to produce the N-amino-2-pyridones in good to excellent yields. The structure of the synthesized compounds were characterized and established on the basis of their spectral data analysis and single-crystal XRD analysis.