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Type: Artigo de periódico
Title: Study of the reactivity of alpha-acylenaminoketones. Synthesis of pyrazoles
Author: Negri, G
Kascheres, C
Abstract: The reactions of 4-(methylamino)-3-penten-2-one with diazoketones yielded the alpha -acylenaminoketones 1-3 in good yields. Preparation of the alpha -acylenaminoketone 4 was carried out by treatment of 4-(t-butylamino)-3-penten-2-one with benzoyl chloride being followed by reaction of transamination with methylamine. The reactions were carried out in five different solvents land were submitted to gas chromatography/mass spectrometry analysis, with the goal of obtaining substituted pyrazoles and determining which of the carbonyls would preferentially be attacked by the nucleophile. The reactions of compounds 1-4 with hydrazine reagents led to the formation of the pyrazoles 5-7a-q. Small amounts of 4-methylamino-2-pentenones 10a-q, amides 11a-q and pyrazoles 12a-q were also obtained in these reactions. The unexpected formation of pyrazoles 15d,h,q was detected when methanol and N,N-dimethylformamide were used as solvents in the reactions of alpha -acylenaminoketone 4 with hydrazine reagents.
Country: EUA
Editor: Hetero Corporation
Citation: Journal Of Heterocyclic Chemistry. Hetero Corporation, v. 38, n. 1, n. 109, n. 123, 2001.
Rights: fechado
Date Issue: 2001
Appears in Collections:Unicamp - Artigos e Outros Documentos

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