25327-42-8

Upstream product

• 131534-24-2 2-amino-4-methyl-4,6-diphenyl-4H-pyran-3,5-dicarbonitrile 
• 5447-87-0 2-(1-phenylethylidene)propanedinitrile 
• 98-86-2 acetophenone 
• 107-91-5 cyanoacetic acid amide 

Downstream Products

• 120131-40-0 6-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-imino-4-phenyl-cyclohex-3-ene-1,1,3-tricarbonitrile 
• 14045-37-5 1,2-dihydro-2-oxo-4-phenylpyridine-3-carbonitrile 
• 120131-42-2 6-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-oxo-4-phenyl-cyclohex-3-ene-1,1,3-tricarbonitrile 

Relevant academic research and scientific papers

Homogeneous and stereoselective copper(II)-catalyzed monohydration of methylenemalononitriles to 2-cyanoacrylamides

A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a Ki-value of 35.7 μM at the Dengue and 44.6 μM at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively.

A study on the scope of the photochemical ring contraction of substituted 2-amino-3-cyano-4H-pyrans to cyclobutenes: Crystal structure of 3-carbamoyl-3-cyano-1-ethoxycarbonyl-4-isopropyl-2-phenylcyclobutene

A study on the influence of substitution on the photochemical reactivity of a series of differently substituted 2-amino-4H-pyrans 10a-h has been carried out. All of the compounds undergo ring contraction to the corresponding cyclobutenes 11a-h on direct irradiation. Variable amounts of the enamides 12 and the alkynes 13 were also obtained, as secondary photoproducts. The results obtained show that the cyclization takes place in reasonable yields with alkyl, phenyl and hydrogen substitution at C-4 and at C-6. Cyano, ethoxycarbonyl and benzoyl substitution at C-5 also promotes the reaction. A high degree of stereochemical control was observed in most cases. The molecular geometry of cyclobutene 11a1 has been established by X-ray diffraction analysis. This study also shows that the crystal packing is formed by a system of chains linked by strong hydrogen bonds.