98276-70-1

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Diacetylpyrazole is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its presence in the molecular structure allows for the development of new drugs with potential therapeutic applications, such as anti-inflammatory, analgesic, and antipyretic properties.
Used in Medicinal Chemistry Research:
3,5-Diacetylpyrazole is utilized as a building block in medicinal chemistry research to explore novel drug candidates. Its unique structure and reactivity enable the design and synthesis of new molecules with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Drug Development:
3,5-Diacetylpyrazole plays a crucial role in drug development, as it can be incorporated into the molecular structure of new drug candidates. This allows researchers to optimize the pharmacokinetic and pharmacodynamic properties of these compounds, leading to the development of more effective and safer medications for various diseases and conditions.

Upstream product

• 2684-62-0 diazoacetone 
• 38302-93-1 (E)-1-bromo-1-buten-3-one 
• 29214-57-1 3-acetylheptane-2,6-dione 
• 96616-83-0 pyrazole-3,5-dicarboxylic acid monopotassium salt 
• 917-54-4 methyllithium 

Relevant academic research and scientific papers

Efficient syntheses of some versatile 3,5-bifunctional pyrazole building blocks

A series of convenient synthetic procedures are reported for pyrazole derivatives with carbonyl or ester groups in the 3- and 5-positions and variable substitution pattern at C4 and at the functional side arms. All compounds have been characterized by 1H and 13C NMR spectroscopy, elemental analyses, and mass spectrometry. In addition, the structures of several pyrazole derivatives have been determined by single crystal X-ray diffraction, which provides insight into the effect of functional side arms on the hydrogen-bonded supramolecular motifs of NH-pyrazoles. Georg Thieme Verlag Stuttgart.

Synthesis and relative stability of 3,5-diacyl-4,5-dihydro-1H-pyrazoles prepared by dipolar cycloaddition of enones and α-diazoketones

An unusual reaction process that produced unexpected heterocyclic systems by a fragmentation-recombination mechanism is described. Thus treatment of the triketone, 3-acetyl-2,6-heptanedione, 1, with methanesulfonyl azide gave, in addition to the expected α-diazo ketone 3a, the dihydro-pyrazole 3c and its oxidation product, the pyrazole 3d. We propose that the initially formed α-diazo ketone 3a fragments into the simple a-diazomethyl ketone and methyl vinyl ketone which then undergo an intermolecular [2,3]-dipolar cycloaddition. Analogous treatment of the trifluoromethyl trione 2 again afforded a pyrazole 4c. Further experiments were carried out to lend evidence to our mechanistic hypothesis. Thus a-diazoacetophenone 5 and MVK underwent a [2,3]-dipolar cycloaddition under mild conditions to give the two regioisomeric dihydropyrazoles 6a and 6b. Interestingly these were formed in a 2:1 ratio, which suggested that 6a was more stable than 6b. The structures of 6a and 6b were optimized by using the B3LYP density functional method and the 6-31G*basis set and isomer 6a was predicted to be 1.5 kcal/mol more stable than isomer 6b. This energy difference could be rationalized by the greater capacity of the acetyl group than the benzoyl group to conjugate with the hydrazone. This difference in conjugation is reflected by key bond length differences. Thus we have discovered a novel fragmentation-cycloaddition process. We have also presented evidence for the mechanism of the formation of the dihydropyrazoles and carried out calculations to support these findings.