Investigation of naphthyridines

The corresponding arylamides were obtained from methyl 2-anilinonicotinate and dimagnesylamines, and the amides were converted to 4-arylamino-2,3-benzo-1,8-naphthyridines by the action of phosphorus oxychloride. The pK_a values of the 2-anilinonicotinic acid arylamides were determined.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 247–248, February, 1974.     

Synthesis and reactions of 3-(N-arylcarbamoyl)-2-methylcinchoninic acid

The Pfitzinger reaction between acetoacetic acid arylamides and the potassium salt of isatinic acid leads in good yield to 3-(N-arylcarbamoyl)-2-methylcinchoninic acids. Refluxing the latter in 2-propanol produced N-substituted imides of 2-methylquinoline-3,4-dicarboxylic acids and, with benzaldehyde in p-xylene in the presence of piperidine, to N-phenylimides of 2-styrylquinoline-3,4-dicarboxylic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 652–653, May, 1988.     

AB Initio and MNDO calculations of atomic interactions in the CH3OCOCl molecule

The CH₃OCOCl molecule is calculated by ab initio methods using the split-valence basis sets at RHF/3-21G//RHF/3-21G, RHF/6-31G^*//RHF/6-31G^*, and RHF/6-311G^*//RHF/6-31G^* levels of theory and in the MNDO approximation. The optimized geometry of the molecule is consistent with the experimental data. The populations of the p-AOs of this molecule and the MO compositions show that the electron distribution in this molecule should be interpreted without considering the conjugation between the lone electron pairs of the Cl or O atoms and the π-electron system of the carbonyl group. The asymmetry parameters of the electric field gradient on the³⁵Cl nucleus were calculated using the Cl p-AO populations and compared with the corresponding experimental value. Instite of Technical Chemistry, Ural Branch, Russian Academy of Sciences. Translated fromZhurnal Struktumoi Khimii, Vol. 37, No. 4, pp. 646–651, July–August, 1996. Translated by I. Izvekova     

Synthesis of 1,2,4-triazolo[4,3-a]quinoline-9-, 1,2,3,4-tetrazolo[4,3-a]quinoline-9 and 1,2,4-triazino[4,3-a]quinoline-10-carboxylic acids from 2-chloro- and 2-hydrazinocinchoninic acids

Treatment of 2-chlorocinchoninic acid with hydrazine gives 2-hydrazinocinchoninic acid and with aroylhydrazines to give 1,2,4-triazolo[4,3-a]quinoline-9-carboxylic acids. These are also prepared by the action of benzoyl chloride or the carboxylic acid on 2-hydrazinocinchoninic acid. With pyruvic acid the latter gives 3-methyl-4-oxo-1,2,4-triazino[4,3-a]quinoline-10-carboxylic acid and with nitrous acid gives 1,2,3,4-tetrazolo[4,3-a]quinoline-9-carboxylic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1227–1229, September, 1991.     

Investigation of naphthyridines. 16. Synthesis of derivatives of 2,5-dioxo-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carboxylic acids from anilides (hydrazides) of 6-oxo-2-styrylnicotinic acids

Heating anilides (hydrazides) of 5-cyano-6-oxo-2-styrylnicotinic acids in polyphosphoric acid (PPA) leads to amides of 7-aryl-2,5-dioxo-6-phenyl(amino)-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carboxylic acids, which on heating with perchloric acid in acetic acid give the corresponding acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1809–1812, December, 2004.For Part 15 see [1].     

Synthesis and properties of 2-(2-oxoindolin-3-ylidene)-2-cyanoacetic acid piperidides and morpholides

The reaction of isatins with cyanoacetic acid piperidide or morpholide gives the corresponding derivatives of 2-(2-oxoindolin-3-ylidene)-2-cyanoacetic acid, which may be reduced to give amides of 2-(2-oxoindolin-3-yl)-2-cyanoacetic acid and react with ethanolic alkali to give quinoline derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.12, pp. 1611–1613, December 1992.     

Synthesis of substituted 2-hydrazino- and 2-(Β-acylhydrazino)-cinchoninic acid amides and their cyclization to 1,2,4-triazolo[4,3-a]quinoline-9-carboxylic acid amides

The reaction of substituted 2-chlorocinchoninic acid amides with hydrazine hydrate or acylhydrazines gave 2-hydrazino- and 2-(-acylhydrazino)cinchoninic acid amides. The latter were also obtained by acylation of the 2-hydrazino derivatives. It is shown that 1,2,4-triazolo[4,3-a]quinoline-9-carboxylic acid amides are formed when 2-hydrazinocinchoninic acid amides are refluxed with formic or acetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 493–496, April, 1991.     

2-Arylamino-3-Cyano-5,6,7,8-tetrahydroquinolines and 2-substituted 1-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]-quinolin-4-ones derived therefrom

Reaction of 2-chloro-3-cyano-5,6,7,8-tetrahydroquinoline with arylamines gives 2-arylamino-3-cyano-5,6,7,8-tetrahydroquinolines, which on reaction with acetic anhydride or benzoyl chloride are converted into the N-acyl derivatives, and on further treatment with hydrogen chloride in anhydrous ethanol, into 2-substituted 1-aryl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-4-ones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 85–87, January, 1988.     

Heterocyclic compounds

A method for the synthesis of 9-arylamino--quinindanes from anilides of cyclopentylideneanthranilic acid has been devised. A number of previously undescribed compounds have been obtained, and their properties have been examined.For Parts I and II, see [1].The name -quinindanes has been suggested for 2, 3-trimethylenequinolines [2].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1242–1243, September, 1970.     

Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.