Synthesis ofN-substituted 2-(5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)glyoxylic acids

Obanin, G. A.; Fokin, A. S.; Burgart, Yanina V.; Ryzhkov, O. V.; Skryabina, Z. É.; Салоутин, В. И.; Чупахин, О. Н.

doi:10.1007/bf02495765

Cited by 4 publications

(5 citation statements)

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“…Esters II and III were synthesized by the procedure described in [1]. Ester IIIc was not reported previously.…”

Section: Methodsmentioning

confidence: 99%

“…IR spectrum, ν, cm -1 : 3103 (CH), 1740 (CO 2 Et), 1666 (COC 6 F 5 ), 1654 (C=N). 1 Following a similar procedure, from 443 mg (1 mmol) of ester IIIc and 0.1 ml (1 mmol) of phenylhydrazine we obtained 307 mg (75%) of compound IVb with mp 127-128°C. …”

Section: Ethyl 3-(4-methoxyphenylaminomethylidene)-24-dioxo-4-pentafmentioning

confidence: 99%

“…According to the NMR data, quinoxalinones Va and Vb, like their acyclic precursors (esters III), in solution exist as mixtures of Z and E isomers [1] differing by orientation of the amino group with respect to the C=C bond.…”

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confidence: 99%

“…Undoubtedly, the latter procedure for the synthesis of pyrazoles IV is more advantageous since 3-arylamino-methylidene-2,4-dioxo-4-pentafluorophenylbutanoates III are usually prepared from 3-ethoxymethylidene-substituted analog II and the corresponding arylamine [1] while the latter is liberated in the synthesis of heterocycles IV from ester III.…”

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confidence: 99%

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3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles

et al. 2005

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3-Ethoxy-and 3-arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates undergo cyclization by the action of hydrazine hydrate and phenylhydrazine to give ethyl 4-pentafluorobenzoylpyrazole-5-carboxylates. The reaction of 3-ethoxymethylidene-2,4-dioxo-4-pentafluorophenylbutanoate with o-phenylenediamine leads to formation of 3-[2-(2-aminophenylamino)-1-pentafluorobenzoylethenyl]-1,2-dihydroquinoxalin-2-one. 3-Arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates react with o-phenylenediamine to afford 3-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)-1,2-dihydroquinoxalin-2-ones and/or 3-(2-arylamino-1-pentafluorobenzoylethenyl)-1,2-dihydroquinoxalin-2-ones.

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“…Esters II and III were synthesized by the procedure described in [1]. Ester IIIc was not reported previously.…”

Section: Methodsmentioning

confidence: 99%

Section: Ethyl 3-(4-methoxyphenylaminomethylidene)-24-dioxo-4-pentafmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles

et al. 2005

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“…Using ethyl 4-(R-amino)-2-oxo-3-pentafluorobenzoyl-but-3-enoate 50, obtained from copper chelate of ethyl pentafluorobenzoyl pyruvate, Nsubstituted 2-(4-oxo-5,6,7,8-tetrafluoro-1,4-dihydroquinolin-3-yl)glyoxylic acids and their esters 52 (Scheme 17) have been synthesized [52]. 3-Arylhydrazones of fluorinated 2,3,4-triketoesters (51, R= Ar), obtained by the coupling reaction of aryldiazonium chlorides with fluoroacyl(aroyl) pyruvates or their chelates, may be used for the synthesis of fluorinated cinnolines.…”

Section: Fluorinated Benzazinesmentioning

confidence: 99%