846022-60-4

Upstream product

• 113463-18-6 C₁₆H₁₆N₂O₂ 
• 100-63-0 phenylhydrazine 
• 832-01-9 methyl p-methoxycinnamate 
• 201230-82-2 carbon monoxide 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 

Downstream Products

• 72606-92-9 3-ethoxy-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole 
• 1338378-18-9 4-chloro-3-ethoxy-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole 
• 1338378-11-2 4-chloro-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-ol 
• 1401696-28-3 5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1401696-38-5 5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl β-D-glucopyranoside 

Relevant academic research and scientific papers

Palladium-catalyzed carbonylative coupling of α-chloroketones with hydrazines: a simple route to pyrazolone derivatives

A range of pyrazol-5-one and pyrazol-3-one derivatives has been synthesized in a single step via a palladium-catalyzed carbonylation of aromatic or aliphatic α-chloroketones, in the presence of aromatic or aliphatic hydrazines. A reaction mechanism, explaining the observed regioselectivity, has been also discussed.

Synthesis, crystal structure, and fungicidal activity of novel 1,5-diaryl-1H-pyrazol-3-Oxy derivatives containing oxyacetic acid or oxy(2-thioxothiazolidin-3-yl)ethanone moieties

A series of novel 1,5-diaryl-1H-pyrazol-3-oxy derivatives containing oxyacetic acid or oxy(2-thioxothiazolidin-3-yl)ethanone moieties were prepared from methyl 3-arylacrylates via a serial of reactions included addition-cyclization, oxidation, substitution, hydrolysis, and condensation. Their structures were confirmed by 1H-NMR, 13C-NMR, IR, and elemental analysis. In addition, the crystal structure of the compound 2-(1,5-diphenyl-1H-pyrazol-3-yloxy)-1-(2-thioxothiazolidin-3-yl)ethanone was determined by single crystal X-ray diffraction analysis. Bioassay results indicated that the compound 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)- 1-(2-thioxo-thiazolidin-3-yl)ethanone exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 μg mL-1.

DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles

A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.

Reactions of 4-alkylidene (arylidene)-1-phenylpyrazolidine-3,5-dione

Reactions of 4-alkylidene(arylidene)-1-phenylpyrazolidine-3,5-dione with oxidizing (chromium trioxide/acetic acid) as well as with reducing (sodium borohydride/methanol) agents were carried out. Phenylhydrazine reacted with 4-arylidene-1-phenylpyrazolidine-3,5-diones via fission of exo C=C bond to give 1-phenylpyrazolidine-3,5-dione and the corresponding aryl hydrazones.