4-hydroxy-2-quinolones. 109. Alkylation of 4-substituted ethyl 2-oxo-1,2-dihydro-quinoline-3-carboxylates

The alkylation of the ethyl esters of 4-methyl, 4-chloro-, and 4-amino substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acid by ethyl iodide in the system DMF/K₂CO₃ has been studied. Features of the structure of the starting compounds and their effect on the ratio of the N-and O-alkyl products formed are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1502–1507, October, 2006.     

4-hydroxy-2-quinolones. 179*. Synthesis,structure, and anti-inflammatory activity of 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-ylacetic acid and its derivatives

The synthesis of 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-ylacetic acid has been carried out and the structure and acid properties studied. Preparative methods for its esterification and amidation are proposed. The anti-inflammatory properties of the synthesized compounds have been evaluated.     

4-Hydroxy-2-quinolones. 168*. Synthesis,chemical and antitubercular properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out.     

4-hydroxy-2-quinolones. 202*. Synthesis, chemical and biological properties of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides

In continuation of the search for potential analgesics amongst 4-hydroxyquinol-2-one derivatives we have proposed and carried out a preparative method of synthesis of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides. It has been shown that bromination of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid allylamide using an equivalent of molecular bromine occurs with a conventional addition of the halogen to the allyl double bond and not with halocyclization. The results of the study of the analgesic properties of the compounds prepared are presented.     

4-hydroxy-2-quinolones. 95. Synthesis, structure, and antitubercular properties of hetarylamides of 4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid

The optimal conditions for obtaining hetarylamides of 4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid are suggested on the basis of derivatographic investigations. The ¹H NMR spectra of the synthesized compounds, their spatial structure, and also the results of a study of their antitubercular properties are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 874–886, June, 2006.     

4-Hydroxy-2-quinolones. 154*. Pyrimidin- 2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydro- quinoline-3-carboxylic acids. synthesis,structure, and properties

The synthesis of a series of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids pyrimidin-2-ylamides has been carried out with the aim of subsequent microbiological investigation. In acetic acid it was found that these compounds are brominated by 1 equivalent of bromine at position 5 of the pyrimidine ring. The only exception is the 1-allyl derivative which undergoes heterocyclization under these conditions to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrimidin-2-ylamide. The results of a study of the antitubercular activity of the synthesized compounds are presented.     

4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides are reduced to the corresponding quinoline-3-carboxamides by zinc in glacial acetic acid but in refluxing triethylphosphite they are converted to the symmetrical N,N′-di(4-hydroxy-2-oxo-1,2-dihydro-3-quinolinoyl)hydrazines. A study of the antitubercular activity of the synthetic compounds has been carried out. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1687–1692, November, 2007.     

Acylpyruvic acid amides and hydrazides: XII. Reaction of 4-Aryl-2-hydroxy-4-oxo-2-butenic acids arylamides with triphenylphosphoranylideneacetic acid esters

4-Aryl-2-hydroxy-4-oxo-2-butenic (aroylpyruvic) acid arylamides react with triphenylphosphoranylidenacetic acid esters to form products of Wittig reaction at α-carbonyl group, the 5-aryl-3-arylaminocar-bonyl-5-oxo-3-pentenoic acid esters. Features in structure of the obtained compounds are discussed.     

4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

Various methods of synthesizing amides of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acids have been studied. Results of investigations on the antitubercular and antiinflammatory activity of the obtained compounds are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 542–555, April, 2006.     

4-hydroxy-2-quinolones. 40. Synthesis and biological properties of anilides of 1H-2-oxo-4-hydroxyquinoline-3-carboxylic acid

An improved method for the synthesis of anilides of 1H-2-oxo-4-hydroxyquinoline-3-carboxylic acid was proposed. Results of the study of antithyroid and anti-tuberculosis activity of the compounds synthesized are presented.For the Communication 39, see [1].National Pharmaceutical Academy of Ukraine, Kharkov 31002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 203–206, February, 2000.     

4-Hydroxy-2-quinolones 113. Synthesis and antitubercular activity of N-R-amides of 4-hydroxy-6-methyl-2-oxo-1-propyl-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid

A preparative method has been developed and the synthesis has been effected of anilides and heterylamides of 4-hydroxy-6-methyl-2-oxo-1-propyl-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid. A comparative analysis has been carried out of the structure and antitubercular properties of the synthesized compounds and their analogs unsubstituted in the quinoline nucleus. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 405–414, March, 2007.     

Reactivity and stereochemical structure of 4-hydroxy- and 4-alkoxyhexahydropyrimidine-2-thiones

Substituted 4-hydroxyhexahydropyrimidine-2-thiones were obtained by the reaction of -isothiocyanatoaldehydes with ammonia or methylamine. When heated with alcohols in the presence of p-toluenesulfonic acids, the synthesized compounds gave the corresponding 4-alkoxyhexahydropyrimidine-2-thiones, which were converted into other 4-alkoxy derivatives by the action of the respective alcohols and were hydrolyzed to the initial 4-hydroxyhexahydropyrimidine-2-thiones by the action of an aqueous solution of oxalic acid or potassium hydroxide. The reaction of the 4-hydroxyhexahydropyrimidine-2-thiones with methyl iodide led to the formation of 2-methylthio-4-hydroxy-3,4,5,6-tetrahydropyrimidine hydriodides. It was shown by PMR spectroscopy that the stereoisomers in which the hydroxyl (or alkoxyl) group has the axial orientation are thermodynamically more stable.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 260–266, February, 1985.     

4-hydroxy-2-quinolones. 191.* synthesis,tautomerism and biological activity of benzimidazol-2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids

A series of benzimidazol-2-ylamides of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids was prepared in a search for biologically active compounds. These compounds exist in the crystal exclusively in the amide form, while in solution amide↔imide tautomerism is observed. The results of a study of the antithyroid and antituberculosis activities of these compounds are given.     

3-氨基-2-羟基-4-苯基丁酸的合成

3-氨基-2-羟基-4-苯基丁酸的合成;乌苯美司;氨基羟基苯基丁酸;合成     

4-Hydroxy-2-quinolones. 92. Reaction of 1-R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines with anilines

A preparative method is proposed and the synthesis of 4-arylamino-2-oxo-1,2-dihydroquinolines has been effected. An X-ray structural investigation of 4-(4-chlorophenylamino)-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylic acid has been carried out enabling the ease of decarboxylating such compounds to be substantiated. Results are given of a study of the anti-inflammatory activity of the synthesized compounds. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–395, March, 2006.     

Synthesis of 4-hydroxy-2-methylisocarbostyril-3-carboxanilides

A procedure for preparing the title compounds is reported. These compounds represent the first 2-substituted-4-hydroxyisocarbostyrils, a structural type which could not be obtained by N-alkylation of the previously known 2H-4-hydroxyisocarbostyril. Although 3-carboxanilides in this series could not be made by aminolysis of the corresponding 3-ester, they were successfully prepared from 4-hydroxy-2-methylisocarbostyril using aryl isocyanates and sodium hydride in hexamethylphosphoramide as solvent. Evidence is presented for an enolic (“4-hydroxy”) form of the title compounds and preference for O-alkylation was observed. Contrary to previous reports, data was obtained to support the enolic structure of the previously known 4-hydroxyisocarbostyril.     

4-Hydroxy-2-quinolones. 152*. 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline and its biologically active derivatives

A synthesis and study of the spatial structure of 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline have been carried. 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids [1-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)ethylidene]hydrazides were prepared from this compound by two routes. A comparative analysis of the antitubercular properties of the synthesized compounds and of the closely structurally related N,N′-di(1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)hydrazines has been performed. *For Communication 151 see [1]. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–222, February, 2009.     

Brominated derivatives of 4-hydroxy- and 4-methoxy-6-methyl-2H-pyran-2-ones

Twenty-five different brominated derivatives of 4-hydroxy-6-methyl-2-pyrone (triacetic acid lactone) and 3-acetyl-4-hydroxy-6-methyl-2-pyrone (dehydroacetic acid) have been prepared. Fifteen derivatives have not been previously described and the preparations of a few known products have been improved. Bromination at C-3, C-5, methyl group at C-6 and deacetylations at C-3 have been the types of reactions used.     

4-hydroxy-2-quinolones. 43. Thermolysis of ethyl esters of 1-R-2-oxo-4-hydroxy-quinoline-3-carboxylic acids

Ethyl esters of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids under thermolysis conditions are converted to 5,9-di-R-6,7,8-trioxodiquinolino[3,4-b;3,4-e]-4H-pyrans. One of the synthesized compounds was studied by X-ray diffraction.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 516–522, April, 2000.     

4-Hydroxyquinolones-2. 91. Synthesis and properties of ethyl 1-R-4-hydroxy-6-methyl-2-oxo-dihydropyridine-5-carboxylates

The reaction of ethyl aminocrotonates with derivatives of malonic acid is a suitable method for the preparation of ethyl 4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-5-carboxylates. One of the synthesized materials has been studied by X-ray crystallography. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, 217–223, February, 2006.