134277-39-7Relevant academic research and scientific papers
Copper-Catalyzed Synthesis of Substituted 4-Acylpyrazole Derivatives through a Cascade Transformation from N-Propargylic Sulfonylhydrazones and Diaryliodonium Salts
Li, Ren-Hao,Fan, Xin-Yang,Hu, Zi-Lin,Liu, Zhi-Kai,Yang, Ying,Tang, Hai-Tao,Chen, Yi-Hui,Chen, Li,Zhan, Zhuang-Ping
, p. 2283 - 2287 (2018)
A concise strategy for the synthesis of substituted 4-acylpyrazole derivatives from N-propargylic sulfonylhydrazones and diaryliodonium salts has been developed. The pyrazole derivatives are formed through a five-step cascade sequence that includes intramolecular cyclization, hydroxylation, elimination, copper-catalyzed aerobic oxidation, and intramolecular rearrangement.
Synthesis of 4-Acylpyrazoles from Saturated Ketones and Hydrazones Featured with Multiple C(sp3)-H Bond Functionalization and C-C Bond Cleavage and Reorganization
Tian, Miaomiao,Shi, Xiaonan,Zhang, Xinying,Fan, Xuesen
, p. 7363 - 7372 (2017/07/26)
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.
Method for synthesizing 4-acyl pyrazole compound from non-cyclic ketone hydrazone
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Paragraph 0070; 0071; 0072, (2017/09/26)
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.
1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides and Nitrile Imines with 2-Methoxyvinyl Phenyl Ketone
Coutouli-Argyropoulou, E.,Thessalonikeos, E.
, p. 429 - 432 (2007/10/02)
Nitrile oxides react regioselectively with 2-methoxyvinyl phenyl ketone 1 to give 4-benzoylisoxazoles 4 via elimination of methanol from the primary cycloadducts 3.After heating with an excess of nitrile oxide bis-cycloadducts 5 were also formed.Reactions
