P. P. Mukovoz

Synthesis and structural features of 3,4,6-trioxoalkanoic acids methyl esters

1,3,4,6-Tetracarbonyl compounds are stable reactive oxo systems that are successfully utilized in organic synthesis for preparation of versatile azaheterocycles, in particular, of those possessing a biological activity [1–6]. The known aryl derivatives of 3,4,6-trioxoalkanoates which are a transition forms between 1,3,4,6-tetraketones [7–10] and 3,4-dioxo-1,6-hexandioates (ketipinates) acid [11–14], remained poorly understood before our research, and the methods of their preparation were limited to the reaction of 5-aryl-2,3-furandiones with 1,1dialkoxyethylenes (ketene acetals) [15] and hydration of 5-aryl-2-acylmethylene-2,3-dihydro-3-furanones [16].

Method of synthesis and structure of (5E)-5-(2-alkoxy-2-oxoethylidene)-4-hydroxy-2,2-dimethyl-1-(4-methylphenyl)-2,5-dihydro-1H-pyrrole-3-carboxylates

A procedure has been developed for the synthesis of dialkyl (5E)-5-(2-alkoxy-2-oxoethylidene)-4-hydroxy-2,2-dimethyl-1-(4-methylphenyl)-2,5-dihydro-1H-pyrrole-3-carboxylates by three-component condensation of dialkyl 3,4-dihydroxyhexa-2,4-dienedioate with acetone and p-toluidine. The structure of the products is discussed on the basis of the IR, 1H NMR, and X-ray diffraction data.

Synthesis and structure of 2,2′-(2-hydroxy-2H-1,4-benzoxazin-2-yl-3-ylidene)diacetic acid esters

Dialkyl 3,4-dioxohexanedioates react with 2-aminophenols to give (2′Z)-2,2′-(2-hydroxy-2H-1,4-benzoxazin-2-yl-3-ylidene)diacetic acid esters. The product structure is discussed on the basis of the IR and 1H NMR spectral data.

Reaction of 3,4-dioxohexane-1,6-dioic acid esters with 2,4-dinitrophenylhydrazine

Reaction was studied of 3,4-dihydroxyhexa-2,4-diene-1,6-dioic acid esters with 2,4-dinitrophenylhydrazine that led to the formation of esters of (3E)-3-[2-(2,4-dinitrophenyl)-hydrazinylidene]-4-oxohexane-1,6-dioic and (3E,4E)-3,4-bis[2-(2,4-dinitrophenyl)hydrazinylidene]-hexane-1,6-dioic acids. The structural features of compounds synthesized were established from the data of IR and NMR spectra and X-ray diffraction (XRD) analysis.

Reaction of methyl 3,4-dihydroxy-6-oxo-2,4-alkadienoates with 2-aminophenol

Methyl [(3Z)-2-hydroxy-3-(2-oxoalkylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-yl]acetates were prepared by reacting methyl 3,4-dihydroxy-6-oxo-2,4-alkadienoates with 2-aminophenol.

Synthesis and Structure of 5-(2-Alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole-3-carboxylic Acid Esters

Dialkyl 3,4-dihydroxyhexa-2,4-dienedioates reacted with substituted anilines and aromatic aldehydes or with the corresponding Schiff bases to give 5-(2-alkoxy-2-oxoethyl)-1,2-diaryl-4-hydroxy-1H-pyrrole- 3-carboxylates.

Reaction of 1,3,4,6-tetraoxo compounds with arylamines and cycloalkylketones

Reactions of methyl 3,4,6-trioxoheptanoate and 1,6-dimethyl-1,3,4,6-tetraoxohexane with aromatic amines (aniline, p-toluidine) and cycloalkylketones (cyclopentanone, cyclohexane, camphor) were studied. The structure of the resulting compounds was studied by IR and NMR spectrosocopy, mass spectrometry, and X-ray diffraction analysis.

Synthesis, structure, and antimicrobial activity of methyl (4-alkanoyl-1,5-diaryl-2-hydroxy-3-oxo-2,3-dihydro-1 H -pyrrol-2-yl)acetates

Reactions of methyl 3,4,6-trioxoalkanoates (3,4-dihydroxy-6-oxo-2,4-alkadienoates) with mixtures of aromatic aldehydes and arylamines or with the corresponding N-(arylmethylidene)anilines afforded methyl (4-alkanoyl-1,5-diaryl-2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrol-2-yl)acetates. The product structure was discussed on the basis of their IR, 1H NMR, and mass spectra and X-ray diffraction data, and their antimicrobial activity against Staphylococcus aureus P-209 and Escherichia coli M17 was evaluated.

Synthesis, structure, and antimicrobial activity of methyl (4-alkanoyl-3-hydroxy-1,5-diaryl-1H-pyrrol-2-yl)acetates

Reactions of methyl 3,4,6-trioxoalkanoates (3,4-dihydroxy-6-oxo-2,4-alkadienoates) with a mixture of arylamines and aromatic aldehydes or with the corresponding arylidenearylamines lead to the formation of methyl (4- alkanoyl-3-hydroxy-1,5-diaryl-1H-pyrrol-2-yl)acetates. Structure of the synthesized compounds is discussed basing on IR, 1H NMR spectroscopy, mass spectrometry, and X-ray diffraction data.

Reactions of 3,4-dihydroxyhexa-2,4-diene-1,6-dioic acid esters with anthranilic acid hydrazide

Reactions of 3,4-dihydroxyhexa-2,4-diene-1,6-dioic acid esters with anthranilic acid hydrazide lead to the formation of 3,4-bis(2-aminobenzoylhydrazono)hexane-1,6-dioic acid esters. Structural features of the synthesized compounds are discussed.