303130-62-3

Upstream product

• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 100-16-3 4-nitrophenylhydrazone 
• 35999-53-2 4,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dione 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1448155-38-1 (E)-butyl 3-(1-(4-nitrophenyl)-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)acrylate 

Relevant academic research and scientific papers

The reaction between hydrazines and β-dicarbonyl compounds: Proposal for a mechanism

The reaction between aryl or heteroarylhydrazines with fluorinated β-diketones (CF3COCH2COR) yields a variety of 3-, 5-, and 3,5-trifluoromethylpyrazoles and 5-trifluoromethyl-5-hydroxy-Δ2-pyrazolines. Twenty-one of such compounds have been isolated and identified by 13C and 19F NMR. Together with the results from the literature they provide a comprehensive overview of the reaction. Semi-empirical calculations at the PM3 level have been used to rationalize these results. The outcome that emerges seems to be that the dehydration of a pair of 3,5-dihydroxypyrazolidines kinetically controls the isomer formed.

Pyrazole formation: Examination of kinetics, substituent effects, and mechanistic pathways

Reaction kinetics for the condensation of 1,3-diketones 1a-o with selected arylhydrazines (aryl = Ph, 4-NO2Ph, 4-CH3OPh, and 2,4-diNO2Ph) was studied using 19F NMR spectroscopy. Product regioselectivity is modulated by reactant ratios, substituents, and acidity. Reaction rates were found to be influenced by substituents on the diketones and on phenylhy-drazines as well as by acidity of the reaction medium with rates varying as much as 1000-fold. Hammett p values for these cyclizations were determined. The reaction was found to be first order in both the diketone and arylhydrazine. The rate-determining step for pyrazole formation shifts as a function of pH. Mechanistic details and reaction pathways supporting these findings are proposed.

The reaction of aryl and heteroarylhydrazines with aryl-trifluoromethyl β-diketones

We report the results obtained when five aromatic or heteroaromatic hydrazines react with six β-diketones bearing trifluoromethyl and aryl substituents. Forty-two compounds have been isolated corresponding to two isomeric trifluoromethyl pyrazoles and the

INHIBITORS AGAINST THE ACTIVATION OF AP-1 AND NFAT

A medicament inhibiting the activation of AP-1 which comprises as an active ingredient a substance selected from the group consisting of a compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof, and a hydrate thereof and a solvate thereof: wherein X represents a connecting group whose number of atoms in the main chain is 2 to 5 (said connecting group may be substituted), A represents hydrogen atom or acetyl group, E represents an aryl group which may be substituted or a hetero aryl group which may be substituted, ring Z represents an arene which may have one or more substituents in addition to the group represented by formula -O-A wherein A has the same meaning as that defined above and the group represented by formula -X-E wherein each of X and E has the same meaning as that defined above, or a heteroarene which may have one or more substituents in addition to the group represented by formula -O-A wherein A has the same meaning as that defined above and the group represented by formula -X-E wherein each of X and E has the same meaning as that defined above.