Summary.
An improved synthesis of cyanoacetophenone is described. Cyanoacetophenone was reacted with dimethylformamide-dimethylacetal and diphenylformamidine to give 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile and 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile. Reaction of 1-dimethylamino-3-oxo-3-phenyl-1-propene-2-carbonitrile with hydrazines gave either 1-substituted 5-amino-4-benzoylpyrazoles or (1-substituted) 4-cyano-5-phenylpyrazoles. Treatment of 1-anilinomethylene-3-oxo-3-phenyl-1-propene-2-carbonitrile with phenylhydrazine also yielded 5-amino-4-benzoyl-1-phenylpyrazole, whereas reaction with unsubstituted hydrazine afforded 4-cyano-5-phenylpyrazole.
Zusammenfassung.
Eine verbesserte Darstellung von Cyanacetophenon wird beschrieben. Cyanacetophenon reagierte mit Dimethylformamid-dimethylacetal bzw. Diphenylformamidin zu 1-Dimethylamino-3-oxo-3-phenyl-1-propen-2-carbonitril und 1-Anilinomethylen-3-oxo-3-phenyl-1-propen-2-carbonitril. Durch Umsetzung von 1-Dimethylamino-3-oxo-3-phenyl-1-propen-2-carbonitril mit Hydrazinen wurden entweder 1-substituierte 5-Amino-4-benzoylpyrazole oder (1-substituierte) 4-Cyano-5-phenylpyrazole erhalten. Reaktion von 1-Anilinomethylen-3-oxo-3-phenyl-1-propen-2-carbonitril mit Phenylhydrazin ergab ebenfalls 5-Amino-4-benzoyl-1-phenylpyrazol, während unsubstituiertes Hydrazin zu 4-Cyan-5-phenylpyrazol reagierte.
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Received May 8, 1998. Accepted (revised) May 28, 1998
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Reidlinger, C., Dworczak, R. & Junek, H. Cyanoacetophenone as a Synthon for 1,4,5-Substituted Pyrazoles. Monatshefte fuer Chemie 129, 1207–1211 (1998). https://doi.org/10.1007/PL00010132
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DOI: https://doi.org/10.1007/PL00010132