Abstract
Reactions of alkyl, halomethyl 2-chlorovinyl ketones with tert-butylhydrazine in the presence of triethylamine afford unsymmetrical 1-(tert-butyl)-3- and -5-disubstituted pyrazoles. The reaction direction is governed by the ketone ability of the nucleophilic substitution of chlorine and of the dehydrochlorination leading to acetylene ketones. 2-Chlorovinyl ketones react with tert-butylhydrazine along two routes giving mixtures of 1-(tert-butyl)-3- and -5-alkylpyrazoles. The content of 3-alkyl-1-(tert-butyl)pyrazole in the formed isomers mixture grows up to 73% with growing length of the alkyl chain of the ketone and up to 87 and 94% at introducing halogen atom in the alkyl fragment of the chloroenone.
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Original Russian Text © V.A. Kobelevskaya, L.I. Larina, A.V. Popov, E.V. Rudyakova, G.G. Levkovskaya, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 242–249.
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Kobelevskaya, V.A., Larina, L.I., Popov, A.V. et al. Synthesis and structure of 1-tert-butyl-substituted 3(5)-alkylpyrazoles from 2-chlorovinyl ketones. Russ J Org Chem 51, 231–239 (2015). https://doi.org/10.1134/S1070428015020177
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DOI: https://doi.org/10.1134/S1070428015020177