78830-52-1

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 768-03-6 Phenyl vinyl ketone 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 17359-82-9 (Z)-N'-(4-chlorophenyl)benzohydrazonoyl chloride 
• 78830-40-7 [(3R,4S)-4-Benzoyl-2-(4-chloro-phenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-3-yl]-phenyl-methanone 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 

Relevant academic research and scientific papers

Method for synthesizing 4-acyl pyrazole compound from non-cyclic ketone hydrazone

The invention discloses a method for synthesizing a 4-acyl pyrazole compound from non-cyclic ketone hydrazine, and belongs to the technical field of organic synthesis. The technical scheme of the invention is characterized in that the method for synthesizing the 4-acyl pyrazole compound from the non-cyclic ketone hydrazine specifically comprises the following steps: dissolving an alpha,beta-saturated ketone compound in a solvent; adding a catalyst, a ligand and an oxidizing agent in sequence; stirring for reacting at the temperature of 100 to 140 DEG C in a nitrogen atmosphere; then, adding the non-cyclic ketone hydrazine into a reaction system; continually reacting at the temperature of 100 to 140 DEG C in an air atmosphere to obtain the 4-acyl pyrazole compound. By adopting the method, the alpha,beta-saturated ketone compound and the non-cyclic ketone hydrazine are subjected to a one-pot multi-step serial reaction under the catalysis of a copper salt to obtain the 4-acyl pyrazole compound; the method has the advantages of easiness and convenience in operation, mild conditions and wide substrate application range, and the suitable for industrial production.

Synthesis of 4-Acylpyrazoles from Saturated Ketones and Hydrazones Featured with Multiple C(sp3)-H Bond Functionalization and C-C Bond Cleavage and Reorganization

In this paper, an efficient and convenient one-pot synthesis of diversely substituted 4-acylpyrazole derivatives via copper-catalyzed one-pot cascade reactions of saturated ketones with hydrazones is reported. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through the dehydrogenation of a saturated ketone and the [2 + 3] cyclization of the enone with hydrazone followed by an aromatization-driven C-C bond cleavage and reorganization. To our knowledge, this is the first example in which the biologically and pharmaceutically important yet otherwise difficult-to-obtain 4-acylpyrazole derivatives are directly prepared from saturated ketones and hydrazones featured with multiple aliphatic C-H bond functionalization and C-C bond cleavage and reorganization. Compared with literature methods, this novel process has advantages such as simple and economical starting materials, a sustainable oxidant, excellent regioselectivity, and good efficiency.

The Cycloaddition of Nitrilimines with 1,2-Dibenzoylethylenes

The cycloaddition of nitrimines with 1,2-dibenzoylethylenes gave an unexpected 1,3-diaryl-4-benzoylpyrazole and benzoic acid, along with an expected cycloadduct, 1,3-diaryl-4,5-dibenzoyl-2-pyrazoline, and its dehydrogenated product, 1,3-diaryl-4,5-dibenzoylpyrazole.The elimination of the benzoyl group from the pyrazoline followed by dehydrogenation was shown to be the course of the unusual reaction.