Synthesis and structure of 1- tert -butyl-substituted 3(5)-alkylpyrazoles from 2-chlorovinyl ketones

Verfasser / Beitragende:
[V. Kobelevskaya, L. Larina, A. Popov, E. Rudyakova, G. Levkovskaya]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/2(2015-02-01), 231-239
Format:
Artikel (online)
ID: 605530971
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024 7 0 |a 10.1134/S1070428015020177  |2 doi 
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245 0 0 |a Synthesis and structure of 1- tert -butyl-substituted 3(5)-alkylpyrazoles from 2-chlorovinyl ketones  |h [Elektronische Daten]  |c [V. Kobelevskaya, L. Larina, A. Popov, E. Rudyakova, G. Levkovskaya] 
520 3 |a 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. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Kobelevskaya  |D V.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Larina  |D L.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Popov  |D A.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Rudyakova  |D E.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
700 1 |a Levkovskaya  |D G.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/2(2015-02-01), 231-239  |x 1070-4280  |q 51:2<231  |1 2015  |2 51  |o 11178 
856 4 0 |u https://doi.org/10.1134/S1070428015020177  |q text/html  |z Onlinezugriff via DOI 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Kobelevskaya  |D V.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Larina  |D L.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Popov  |D A.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Rudyakova  |D E.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Levkovskaya  |D G.  |u Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/2(2015-02-01), 231-239  |x 1070-4280  |q 51:2<231  |1 2015  |2 51  |o 11178