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Козьминых, В. О.; Игидов, Н. М.; Козьминых, Е. Н.

doi:10.1023/a:1015660009406

Cited by 7 publications

(11 citation statements)

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“…On the other hand, 3a and glycine were produced with a similar pathway involving amino acid SCHEME 4 Reaction pathway of [5] for Wittig reactions of 2,3-dihydrofuran-2,3-diones with Wittig reagents. moiety, the corresponding N-acetic acid substituted 2,3-dihydro-1H-pyrrol-3-one (5d) in methanol, and the presence of pyridine (Scheme 6).…”

Section: Resultsmentioning

confidence: 99%

2,4,5-Substituted furan-3(2H)-ones: Synthesis, reactions with amino acid and hydrazine derivatives

et al. 2005

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Section: Resultsmentioning

confidence: 99%

2,4,5-Substituted furan-3(2H)-ones: Synthesis, reactions with amino acid and hydrazine derivatives

et al. 2005

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“…The IR spectra were obtained in thin layers of vaseline oil on a Specord M-80 spectrometer. The initial 2-(2-oxoethylidene)furan-3(2H)-ones 1a,b were obtained by the method described in [7,8].…”

Section: Methodsmentioning

confidence: 99%

“…To a solution of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate (1a) (1.15 g, 5 mmol) [7] or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one (1b) (1.55 g, 5 mmol) [8] in ethanol (70-80 ml) we added a solution of benzoic isopropylidenehydrazide (0.88 g, 5 mmol) or p-nitrobenzoic isopropylidenehydrazide (1.10 g, 5 mmol) in ethanol (30-40 ml). The mixture was boiled for 15-20 min, and the precipitated pyridazinones 2a-d were filtered off and recrystallized from ethanol or acetonitrile.…”

Section: Reaction Of 2-(2-oxoethylidene)-5-phenylfuran-3(2h)-ones 1amentioning

confidence: 99%

Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

Козьминых

Oborin

Goncharov

et al. 2007

Chem Heterocycl Comp

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Keywords: 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones, 2-(2-oxoethylidene)furan-3-(2H)-ones, reactions with benzoic and p-nitrobenzoic isopropylidenehydrazides.The reactions of 2-ylidenefuran-3(2H)-ones with hydrazine or arylhydrazines lead to the formation of hydrazino derivatives of 3-oxofuran [1], 3-acylpyrazoles [2-4], or 3-alkyl(ylidene)-substituted pyridazine-4(1H)-ones [4]. It is known that the action of aroylhydrazines on 3-oxofuran-2(3H)-ylideneacetates leads to the formation of 1-aroylamino-2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrol-2-ylacetic esters [5]. Other reactions of acyl or ylidene derivatives of hydrazine with five-membered 2-ylidene-2,3-dihydro-3-oxo heterocycles had not been studied before our investigations.As a result of the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate (1a) or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one (1b) with benzoic or p-nitrobenzoic isopropylidenehydrazides we unexpectedly obtained preparative yields of the previously unknown stable cyclic O,N-acetals -3-hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones 2a-d. Equilibrium tautomeric forms C (5) H (A) and C (5) H 2 (B) were detected in solutions of compounds 2c,d in DMSO-d 6 .When the isopropylidenehydrazides of carboxylic acids are brought into reaction with 2-(2-oxoethylidene)furan-3(2H)-ones 1 nucleophilic attack by the NH group of the equilibrium enamino form NH-CMe=CH 2 of the reagent probably occurs at the C (5) atom of the ring in the substrate 1 with subsequent intramolecular heterocyclization of the enehydrazinocarbonyl intermediate, hydrolytic elimination of a molecule of acetone, and the formation of 3-hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones 2. The regioselectivity of NH-nucleophilic attack by the hydrazides at the electron-deficient center C (5) of compounds 1 during the theoretically possible attack also at the C (2) , C (2') , or C (3) atoms confirms the probable orbital control of the reaction [6]. __________________________________________________________________________________________

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“…However, as a rule, they do not possess significant antimicrobial activity [11,12]. By analogy with acylpyruvic acid derivatives, it can be assumed confidently that modification of the 1,3,4,6-tetraoxo structure by intro-ducing halogens into the dicarbonyl fragments will produce noticeable bacteriostatic activity.…”

mentioning

confidence: 99%

“…The structures of the prepared compounds were confirmed by spectral data and comparison with starting substrates III and IV. The antimicrobial activity of halogenated V -VIII was compared with that of structural analogs, known tetraketones III [11,12] and compounds IV [14].…”

mentioning

confidence: 99%

1,3,4,6-tetracarbonyl systems. Part 8. Synthesis and antimicrobial activity of 2(5)-halogenated derivatives of 1,3,4,6-tetracarbonyl compounds

2008

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A series of 1,6-disubstituted 2,5-dibromohexan-1,3,4,6-tetraones and 2,2,5,5-tetrahalogenohexan-1,3,4,6tetraones have been obtained by the treatment of 1,6-disubstituted hexane-1,3,4,6-tetraones with bromine and chlorine. Bromination of (4Z)-6-aryl-3,4-dihydroxy-6-oxohexa-2,4-dienamides led to (2Z,4E)-2-aminocarbonyl-6-aryl-5-bromo-3,4-dihydroxy-6-oxohexa-2,4-dienoates and 6-aryl-2,5-dibromo-3,4,6-trioxohexanamides in preparative yield. The proposed structures of the reaction products were confirmed by IR, UV, 1 H and 13 C NMR, and mass spectrometry. The bacteriostatic activity and acute toxicity of the synthesized compounds have been studied. 513 0091-150X/08/4209-0513

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Cited by 7 publications

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2,4,5-Substituted furan-3(2H)-ones: Synthesis, reactions with amino acid and hydrazine derivatives

2,4,5-Substituted furan-3(2H)-ones: Synthesis, reactions with amino acid and hydrazine derivatives

Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

1,3,4,6-tetracarbonyl systems. Part 8. Synthesis and antimicrobial activity of 2(5)-halogenated derivatives of 1,3,4,6-tetracarbonyl compounds

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