Reaction of hydrazones derived from electron-deficient ketones with Vilsmeier-Haack reagent
Abstract: Reaction of hydrazones derived from ketones bearing an acceptor substituent adjacent to the carbonyl group (α,α,α-trifluoroacetone and ethyl pyruvate) with Vilsmeier-Haack reagent was studied. In most cases, the method allows for regioselective preparation of 1,3-disubstituted pyrazole-4-carbaldehydes – the products of initial C-electrophilic attack, although in one case, the product resulting from concurrent N- and C-attacks of the electrophile at the hydrazone moiety is observed. Under analogous conditions, the reaction of N-arylhydrazone derived from butanedione leads to the formation of 3-chloro-3-(1-arylpyrazol-3-yl) acrylaldehyde – the product of double formylation at both ketone and hydrazone moieties of the starting material.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Reaction of hydrazones derived from electron-deficient ketones with Vilsmeier-Haack reagent ; volume:20 ; number:6 ; year:2014 ; pages:351-354 ; extent:4
Heterocyclic communications ; 20, Heft 6 (2014), 351-354 (gesamt 4)
- Creator
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Ivonin, Sergey P.
Kurpil’, Bohdan B.
Grygorenko, Oleksandr O.
Volochnyuk, Dmitry M.
- DOI
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10.1515/hc-2014-0176
- URN
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urn:nbn:de:101:1-2501130551090.739281246635
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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2025-08-15T07:22:55+0200
Data provider
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Ivonin, Sergey P.
- Kurpil’, Bohdan B.
- Grygorenko, Oleksandr O.
- Volochnyuk, Dmitry M.
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Asymmetric Copper Hydride Catalyzed Coupling Reaction to Access Chiral Ketones
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Synergistic Copper‐Aminocatalysis for Direct Tertiary α‐Alkylation of Ketones with Electron‐Deficient Alkanes
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Zinc-Catalyzed Asymmetric Mannich Reaction Forming β-Amino Ketones
Asymmetric Copper Hydride Catalyzed Coupling Reaction to Access Chiral Ketones
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