ISSN 0005-2531 (Print) ISSN 2522-1841 (Online)
NEW SYNTHESIS OF 3- AND 1,3-PYRAZOLE DERIVATIVES BASED ON 1-CYCLOALKYL-2,3-DICHLORO-1-PROPANONES
E.I.Mammadov, V.A.Huseynova, S.T.Mekhtieva, S.Q.Ismayilova

1-Cycloalkyl-2-propene-1-ones were synthesized by electrophilic addition of cycloalkanecarboxylic acid chlorides and its mono- and dichloride-substituted derivatives to ethylene in the presence of an AlCl3 catalyst at a temperature of –10 ÷ –150C in a dichloroethane medium. The resulting vinyl ketones were converted by chlorination in CCl4 at  –50C to the corresponding 1-cycloalkyl-2,3-dichloro-1-propanones, which form 1-R´-3-cycloalkylpyrazoles with hydrazine and phenylhydrazine in ethanol or toluene. The structure of the obtained pyrazoles was confirmed by the data of IR and H1NMR spectra and the determination of physical-chemical constants. Thus, preparative methods for the synthesis of 3- and 1,3-pyrazole derivatives have been developed for the first time

doi.org/10.32737/0005-2531-2022-4-89-94

 

Keywords : cycloalkanecarboxylic chlorides; 1-cycloalkyl-2-propene-1-ones; 1-cycloalkyl-2,3-dichloro-1-propanones; 3- and 1,3-substituted pyrazoles; electrophilic addition reaction; chlorination of vinylketones
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