Halogenation of fluoroalkyl-substituted ?-ketoesters

Салоутин, В. И.; Skryabina, Z. É.; Rudaya, M. N.; Pashkevich, K. I.

doi:10.1007/bf01141716

Cited by 3 publications

(4 citation statements)

References 6 publications

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“…Chlorination of 3-oxo esters (1) with equimolar amounts of chlorine gives stable 2-chloro-3-fluroalkyl-3-oxopropionates (13). 26,27 According to IR and NMR, esters (13) exist as a tautomer mixture of keto and enol forms. 27 Opposite to 2-chloro-3-oxo esters (13),…”

Section: Methodsmentioning

confidence: 99%

“…In the reaction with the substituted hydrazines non-symmetrical monofluoroalkyl-containing 1,3-diketones (2) can form isomeric 3-R F or/ and 5-R F -pyrazoles (29,30) or/ and their precursors 5-hydroxy-5-fluoroalkylpyrazolines (27) or hydrazones (30) depending on non-fluorinated substituent, the reaction conditions and hydrazine type (Scheme 10). 5, 6, 35 The condensations of 2-hydroxyimino-1,3-diketones (3) with hydrazines produce 4-nitrosopyrazoles (35) and with phenylhydrazine furnish 5-hydroxy-4-hydroxyimino-1-phenyl-5-fluoroalkylpyrazolines (36) (Scheme 12).…”

Section: Reactions With α-Dinucleophilesmentioning

confidence: 99%

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Fluorine-Containing 2-Functionalized 1,3-Dicarbonyl Compounds for Heterocyclic Synthesis

Салоутин¹,

Burgart²,

Чупахин³

2006

HETEROCYCLES

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Section: Methodsmentioning

confidence: 99%

Section: Reactions With α-Dinucleophilesmentioning

confidence: 99%

Fluorine-Containing 2-Functionalized 1,3-Dicarbonyl Compounds for Heterocyclic Synthesis

Салоутин¹,

Burgart²,

Чупахин³

2006

HETEROCYCLES

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“…Bis(ethyi 2-cyanor3~hydroxy-3-pentafluorophenylprop-2-enoato)copper (8). were mixed with 1.2-dibromoethane (0.3 mL) in 5 mL of anhydrous EtOH.…”

Section: Bis(ethylmentioning

confidence: 99%

“…Thus the reaction of pedluoropentanoyl fluoride 4 with ester 1 in the presence of Et3N in anhydrous benzene yielded ester 10, which was isolated via copper chelate 7 (see Table 1, Scheme 1). Analogously, ester 11 and its copper chelate (8) were obtained by acylating ethyl cyanoacetate with pentafluorobenzoyl chloride (5) in the presence of Mg(OEt)2. The use of Et3N as a catalyst in this reaction did not result in the expected product.…”

mentioning

confidence: 99%

Synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxylates. Reactions with nucleophiles

et al. 1999

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Fluorine-containing alkyl 2-cyano-3-oxocarboxylates were synthesized for the first time by the reaction of ethyl cyanoacetate with fluorine-substituted carboxylic acid halides or alkyl earboxylates. The reactions with hydrazine hydrate, phenylhydrazine, and o-phenylenedianaine give hydrazinium (ammonium) enolates or products of acid decomposition.Key words: alkyl perfluoro-2-cyano-3-oxocarboxylates, acylation, condensation, hydrazinc hydrate, phenylhydrazine, o-phenytenediamine, salt formation, acid decomposition.Ethyl 2-cyanoacetoaeetate can be obtained by the reactions of sodium ethyl acetoacetate with C1CN ! or of ethyl cyanoacetate (1) with ketene. 2,3 The most common and convenient method for the synthesis of this 2-cyano-3-oxo ester and its nonfluorinated analogs is acylation of ester ! with the corresponding acid chlorides 4.5 and anhydrides. 6 Ethyl 2-cyanoacetoacetate reacts with NH 3, EtNH2 ,I and semicarbazide 4 to give azomethines in the form of [3-aminocrotonic acid derivatives. Literature data on the synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxytates and their reactivity are lacking.The goal of the present investigation is to obtain new esters of fluorinated 3-oxocarboxylir acids. Among the representatives of this class and their derivatives, many substances were found to possess useful properties for practical purposes. Ethyl-perfluoro=2=cyano-3-oxocarboxylates and their copper chelates were synthesized for the first time, and their reactions with N-nucleophiles (hydrazine hydrate, phenylhydrazine, and o-phenylenediamine) were studied.

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Halogenation of Fluorinated 1,3,5‐Triketones

Sevenard

Kazakova

Chizhov

et al. 2007

Helvetica Chimica Acta

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The behavior of linear and cyclic fluorinated 1,3,5-triketones and their metal derivatives towards common halogenating agents was examined, and optimal reaction conditions for the straightforward synthesis of mono-, di-, and tetrahalogenated products were found (Schemes 1 -3). An aromatization through a double HBr elimination from an a,a'-dibrominated cyclohexanone was shown to be a promising synthetic route to 1,1'-(2-hydroxy-1,3-phenylene)bis[2,2,2-trifluoroethanones] (= 2,6-bis(trifluoro-A C H T U N G T R E N N U N G acetyl)phenols; Scheme 4). Additionally, the 1,3,5-triketones prepared add readily H 2 O or alcohols to produce novel bridged 2,6-dihydroxypyran-4-ones (Scheme 2). The structure of the obtained compounds 6a and 7a was confirmed by X-ray structure analysis.

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Halogenation of fluoroalkyl-substituted ?-ketoesters

Cited by 3 publications

References 6 publications

Fluorine-Containing 2-Functionalized 1,3-Dicarbonyl Compounds for Heterocyclic Synthesis

Fluorine-Containing 2-Functionalized 1,3-Dicarbonyl Compounds for Heterocyclic Synthesis

Synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxylates. Reactions with nucleophiles

Halogenation of Fluorinated 1,3,5‐Triketones

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