Reaction Of Β-dicarbonyl Compounds Research Articles

Synthesis, Characterization, Antimicrobial and Anticarcinogenic Activity of Quinazoline Derivatives

The reaction of β-dicarbonyl compounds as ethyl acetoacetate with hydrazines is a well-established route for the creation of pyrazole derivatives. In this research, 4-hydrazinoquinazoline (4) reacted with ethyl acetoacetate in boiling ethanol it gives ethyl 3-oxobutanoate quinazolin-4-yl-hydrazone (5). Cyclization of the compound (5) in the presence of glacial acetic acid is passed to form 4-(5-hydroxy-3-methyl-1H-pyrazol-1-yl)quinazoline(6). Furthermore, the reaction of phenylisothiocyanate compounds with hydrazines is a well-established way for the synthesis of tetrazinoquinazoline (8). The new compounds are confirmed by elemental analysis, nuclear magnetic resonance, infrared, and mass spectra. In-vitro anti-tumor evaluation of the new compounds across three cell lines HepG2 (liver carcinoma), HCT-116 (colon carcinoma), and MCF-7 (breast carcinoma) indicats high anti-tumor activity. In addition, antimicrobial activity of specific synthesized compounds are screened against four bacterial species. Amongst four, two Gram-negative are Escherichia coli, Pseudomonas aeuroginosa and gram-positive as Staphylococcus aureus and Bacillus subtilis. The antibacterial activity of Compounds (5) and (6) are greater comparing to standard drug (Amphicillin).

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β‐Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron‐Based Oxidants

Selectivity of sulfonylation of β‐keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α‐Sulfonyl β‐keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α‐sulfonyl esters – the products of successive sulfonylation‐deacylation. When β‐diketones are applied as starting materials, only α‐sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α‐sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation‐deacylation. Participation of the solvent in the reaction pathway determines the products structure.

Synthesis and calcium channel antagonist activity of new symmetrical and asymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines

New symmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-di-hydropyridines were synthesized in moderate to good yields via the modified Hantzsch reaction of β-dicarbonyl compounds with (Z)-3-chloro-3-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)acrolein in the presence of an excess amount of NH4OAc. Also, the reaction of β-dicarbonyl compounds with (Z)-3-chloro-3-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)acrolein in the presence of enamino esters and ketones was performed, and asymmetrical 4-[2-chloro-2-(4-chloro-6-methyl-2-oxo-2H-pyran-3-yl)vinyl]-substituted 1,4-dihydropyridines were obtained in moderate to good yields at room temperature. The calcium channel blocking activity of these compounds was assessed. They demonstrated moderate to weak effects, although one compound had a comparable effect (IC50 =1.40×10−7 M) with respect to the reference drug Nifedipine.

Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds

The reaction of β-dicarbonyl compounds (β-ketoesters and β-diketones) with 0.34 mol equiv of trichloro- and tribromoisocyanuric acids produced regioselectively the corresponding α-monohalo β-dicarbonyl compound. On the other hand, utilization of 0.68 mol equiv of the trihaloisocyanuric acid produced the α,α-dihalo β-dicarbonyl compound.

A new synthesis of 1,3-aminols from direct double reduction of β-enamino ketones formed in situ by reaction of β-dicarbonyl compounds with anilines

A new one-pot synthesis of 1,3-aminols by direct reduction of β-enamino ketones, formed in situ by reaction of easily available β-dicarbonyl compounds, with anilines were described. In the case of aliphatic amines such as benzyl amine, n-butyl amine and β-hydroxy ethyl amine, the corresponding 1,3-minols were not obtained. In fact, the β-enamino ketone formed was failed to accomplish further reduction to 1,3-aminol. This approach is the most direct available method for the synthesis of 1,3-aminols.

Regioselective Enamine Formation from Oxonia‐Boranuida‐Betaines and Their Application in Asymmetric Michael Reactions.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of pyrazolo[1,5-a]pyrimidines by the reaction of β-dicarbonyl compounds with 3,5-diamino-4-nitropyrazole

The reaction of 3,5-diamino-4-nitropyrazole with asymmetrical β-dicarbonyl compounds gave polysubstituted pyrazolo[1,5-a]pyrimidines, which are used in reactions with both nucleophilic and electrophilic reagents. The structure of the compounds obtained was demonstrated by x-ray diffraction structural analysis.

Reactions of β-dicarbonyl compounds with acyl cyanides catalyzed or promoted by metal centres in the homogeneous phase

The C–C bond-forming reaction between β-dicarbonyl compounds and acyl cyanides is catalyzed by nickel acetylacetonate or promoted by tin tetrachloride. Thus, β-diketones react with acyl cyanides in the presence of catalytic amounts of [Ni(acac)2] to give β-enamino diketones 3. β-Enamino keto esters 8 or β-enamino diesters 9 are obtained in the reactions of methyl acetoacetate or methyl malonate with acyl cyanides in the presence of stoichiometric amounts of SnCl4. The reactions of acyl cyanides with methyl malonate also afford furanone derivatives 10, whose structure has been determined, in one case, by a single-crystal X-ray analysis. β-Keto amides react with acyl cyanides to give pyrrolidine derivatives 13 both under catalytic conditions and stoichiometric conditions where an equimolar equivalent of promoter was used.

ChemInform Abstract: A New Type of Reaction of β‐Dicarbonyl Compounds: Transformation of Dibenzoylchloromethane (I) to 2‐Chloro‐3‐phenylindenone (III) with SbCl5 as the Reagent.

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Simple Synthesis of 3a,6a-Dihydrofuro [2,3-b]furan Derivatives via the Reaction of β-Dicarbonyl Compounds with 5-Cyano- and 5-Methoxycarbonyl-2-nitrofurans1

Enolates of ß-dicarbonyl compounds react with 5-cyano- and 5-methoxycarbonyl-2-nitrofurans 1a and 1b, respectively, giving products of cine substitution of the nitro group. Their enolates add intramolecularly to the furan ring to give 4-alkoxycarbonyl-3a,6a-dihydrofuro[2,3-b]furan derivatives 2-6 as the ultimate products.

Surface co-ordination reactions of β-dicarbonyl compounds with metallic copper

Surface co-ordinations of dibenzoylmethane, acetylacetone and ethyl acetoacetate with metallic copper in the presence of air have been studied by the use of surface-enhanced Raman scattering, X-ray photoelectron and infrared spectroscopies. Oxygen coadsorbed on the copper surface promoted the reactions through cleavage of the methylene C–H bond. It was found that metallic copper could promote these surface reactions with dicarbonyl compounds, while copper in higher oxidation states appeared to be inactive under the same conditions.

The reaction of β-dicarbonyl compounds with trifluoromethyl-sulphenyl chloride Part II. The synthesis of 3-SCF 3 substituted 2- and 4-quinolinones

3-SCF 3 substituted 4-methyl-2(1H)-, 4-phenyl-2(1H)-, 2-methyl-4(1H), and 2-phenyl-4(1H)-quinolinones were obtained by cyclization of the respective -SCF 3 submitted acetoacetanilides or benzoylacetanilides or their β-phenylimino analogues in concentrated sulphuric acid upon heating. The structures of the compounds obtained were elucidated by elemental analysis and their IR, 1H and 19F NMR, and mass spectra.

The reaction of β-dicarbonyl compounds with trifluoromethylsulphenyl chloride. Part I. CF 3S-substituted esters, anilides of β-keto acids, and their Schiff bases: Synthesis and stability.

The reactions of the β-keto acid derivatives with trifluoromethylsulphenyl chloride were carried out to give the α-SCF 3 substituted esters, anilides, and their Schiff bases of acetyl- and benzoylacetic acids. Ethyl esters of α-(trifluoromethylthio)acetoacetic and α-(trifluoromethylthio)benzoylacetic acids heated in dimethylsulphoxide/water solution give trifluoromethylthioacetone and ω-(trifluoromethylthio)acetophenone respectively, whereas with potassium hydroxide solution they form trifluoromethylthioacetic acid in a good yield.

Studies on the reactions of bis(acetylacetonato)platinum(II) with Lewis bases : V. Reactions of β-dicarbonyl compounds with central carbon-bonded acetylacetonato complexes of platinum(II) and palladium(II)

Central carbon-bonded acetylacetonato complexes of platinum(II) and palladium(II) [M(acac)(γ-acac)PPh 3], I (M = Pt and Pd), reacted with β-dicarbonyl compounds (Hdik) to give three types of complexes according to the nature of the β-dicarbonyl compounds employed; dimethyl malonate and methyl and ethyl acetoacetates yielded [M(acac)(γ-dik)PPhP 3], II, whereas dibenzoylmethane afforded [M(dik)(γ-acac)PPh 3], IV, exclusively. The reaction of benzoylacetone with I afforded a mixture of [M(dik)(γ-dik)PPh 3], III, and IV. The selectivity of the reaction seems to be correlated with the enol- or keto-favoring character of the respective β-dicarbonyl compounds.