期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 253, 期 -, 页码 -出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2021.109932
关键词
Pyrazole; Pyridazinone; B-diketonate; B-diketohydrazone; Furan-3(2H)-one
资金
- Russian Academy of Sciences [AAAA-A19-119011790132-7]
In this study, fluorinated lithium beta-diketonates reacted with hydrazines to form pyrazoles, pyridazinones, and beta-diketohydrazones, and solvent-induced regioisomeric and heterocyclic ring size-controlled formation was observed. Acid-catalyzed cyclocondensation in ethanol yielded fluoroalkylated acetyl NH-pyrazoles or substituted 5-R-F-pyrazoles, while acetyl-containing 3-CF3-pyrazoles were isolated in methanol solvent due to inverse nucleophilic attack of arylhydrazines.
Fluorinated lithium beta-diketonates bearing a methyl acetal group behave in the condensation reactions with hydrazines as trielectrophilic building blocks for the preparation of pyrazoles, pyridazinones and beta-diketohydrazones. For the first time, solvent-induced regioisomeric and heterocyclic ring size-controlled formation was observed for 1,2,4-triketone analogues. Fluoroalkylated acetyl NH-pyrazoles or substituted 5-R-F-pyrazoles were obtained from the acid-catalyzed cyclocondensation of lithium beta-diketonates with (aryl)hydrazines in ethanol. In methanol solvent acetyl-containing 3-CF3-pyrazoles were isolated because of inverse nucleophilic attack of arylhydrazines. The use of aprotic acetonitrile in the condensation resulted in regioselective trifluorinated pyridazinones and fluorinated beta-diketohydrazones formation via initial acetal fragment interaction with N,N-dinucleophile.
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