Reaction of 3-(polyfluoroacyl)chromones with hydrazines: new regioselective synthesis of RF-containing pyrazoles

Reactions of 3-(polyfluoroacyl)chromones with hydrazine, methyl-and phenylhydrazines proceed by the mechanism of nucleophilic 1,4-addition with subsequent pyrone ring opening and heterocyclization at the polyfluoroacyl group to 4-(2-hydroxyaroyl)-3-polyfluoro-alkylpyrazoles or at the aroyl group to...

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Bibliographic Details
Published inRussian chemical bulletin Vol. 57; no. 10; pp. 2146 - 2155
Main Authors Sosnovskikh, V. Ya, Irgashev, R. A., Moshkin, V. S., Kodess, M. I.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.10.2008
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
hydrazines
R
containing pyrazoles
nucleophilic 1,4-addition
X-ray diffraction study
heterocyclization
3-(polyfluoroacyl)chromones
hydrazones
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Summary:Reactions of 3-(polyfluoroacyl)chromones with hydrazine, methyl-and phenylhydrazines proceed by the mechanism of nucleophilic 1,4-addition with subsequent pyrone ring opening and heterocyclization at the polyfluoroacyl group to 4-(2-hydroxyaroyl)-3-polyfluoro-alkylpyrazoles or at the aroyl group to 4-polyfluoroalkyl-2,4-dihydrochromeno[4,3- c ]pyrazol-4-ols. Regiochemistry of the products was established based on the data of 2D-experiments HSQC, HMBC, and NOESY and X-ray diffraction study.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-008-0291-5