G. A. Gevorgyan

Synthesis and Antibacterial Activity of 2-[2,2-Dimethyl-4(3-Trifluoromethylphenyl)-Tetrahydropyran-4-Yl]Arylamine Oxalates

Interaction of ethylcyano(2,2-dimethyltetrahydro-2H-puran-4-yl)acetate with 3-trifluoromethylphenylmagnesium bromide yielded cyanoesters, decarbethoxylation of which produced the corresponding nitrile. Reduction of the latter with LiAlH4 led to the formation of 2-[2,2-dimethyl-4-(3-trimethylphenyl)tetrahydropyran-4-yl]ethylamine. Interaction of the resulting amine with aromatic aldehydes produced azomethines, which were reduced with NaBH4 to secondary amines, which were then converted to the oxalates. Several of these were found to have high levels of antibacterial activity.

Synthesis and some transformations of γ-(p-fluorophenyl)-γ-(2-furyl)propylamine

Ethyl α-cyano-β-(p-fluorophenyl)-β-(2-furyl)propionate was obtained by the condensation of ethyl α-cyano-β-(2-furyl)acrylate with p-fluorophenylmagnesium bromide. Its deethoxycarbonylation led to β-(p-fluorophenyl)-β-(2-furyl)propionitrile. Reduction of the nitrile with lithium aluminum hydride gave γ-(p-fluorophenyl)-γ-(2-furyl)propylamine. Some transformations of the latter were studied.

Acylation of amines and pyrazole with [2-isopropyl-4-(o-methoxyphenyl)-tetrahydropyran-4-yl]acetyl chloride

[2-Isopropyl-4-(o-methoxyphenyl)tetrahydropyran-4-yl]acetic acid has been obtained by the hydrolysis of previously synthesized [2-isopropyl-4-(o-methoxyphenyl)tetrahydropyran-4-yl]acetonitrile. The acyl chloride prepared from this acid gave new amides and 1-acylpyrazole upon interaction with various amines and with pyrazole.

Synthesis and Some Transformations of 2-(3-Amino-1-Phenylpropyl)furan

A preparative method was developed for the synthesis of ethyl furfurylidenecyanoacetate. Its condensation with phenylmagnesium bromide gave ethyl α-cyano-β-(2-furyl)hydrocinnamate, the decarboxylation of which led to β-(2-furyl)hydrocinnamonitrile. Reduction of this nitrile with lithium aluminum hydride gave 2-(3-amino-1-phenylpropyl)furan. Some of its transformations were studied.

Synthesis of 2,6-Diisopropyltetrahydro-2H-4-pyranone and Some Its Substituted Amino Derivatives

Cyclization of 2,8-dimethylnona-3,6-diene-5-one furnished 2,6-diisopropyltetrahydro-2H-4-pyranone. The condensation of the latter with alkylaryl and aliphatic amines afforded azomethines, which were converted into the corresponding amines by reduction with sodium borohydride.

Synthesis and some transformations of 2-(4-isopropyl-2-methyl-2-ethyltetrahydro-2H-pyran-4-yl)ethanamine

Condensation of 2-(4-isopropyl-2-methyl-2-ethyltetrahydro-2H-pyran-4-yl)ethanamine with aromatic aldehydes and ketones and subsequent reduction of the azomethines formed gave secondary amines of the tetrahydropyran series. Reaction of the latter with acetic acid and propionic acid chlorides provided the corresponding amides.

Synthesis and Various Biological Properties of 3-(4-Benzylpiperizino)-1-(4-Ethoxyphenyl)-1-Alkyl(Aryl)-2-Phenylpropan-1-OL Dihydrochlorides

Aminomethylation of 1-(4-ethoxyphenyl)-2-phenylethanone yielded 3-(4-benzylpiperazin-1-yl)-1-(4-ethoxyphenyl)-2-phenylpropan-1-one. Reduction of this compound with lithium aluminum hydride produced 3-(4-benzylpiperazin-1-yl)-1-(4-ethoxyphenyl)-2-phenylpropan-1-one, and interaction of this with Grignard reagents produced 3-(4-benzylpiperazinyl)-1-(4-ethoxyphenyl)-1-alkyl(aryl)-2-phenylpropan-1-ones. Some of the dihydrochlorides of the resulting compounds were found to have anti-inflammatory, analgesic, and peripheral n-cholinolytic activity.

Synthesis of 3-(4-fluorophenyl)-3-(furan-2-yl)propanoic acid and 5-[2-(4-fluorophenyl)-2-(furan-2-yl)ethyl]-1,3,4-oxadiazole-2-thiol derivatives

Synthesis of 3-(4-fluorophenyl)-3-furan-2-ylpropionyl chloride has been performed, and selected transformations of the product have been studied.

Synthesis of 1-(4-butoxyphenyl)-1-cyclohexyl-3-(4-arylpiperazin-1-yl)-2-phenylpropan-1-ols and their dihydrochlorides

Aminomethylation of 1-(4-butoxyphenyl)-2-phenylethanone with paraformaldehyde and substituted piperazines in ethanol medium results in 1-(4-butoxyphenyl)-3-(4-R-piperazin-1-yl)-2-phenylpropan-1-ones. The latter react with cyclohexylmagnesium halide to give 1-(4-butoxyphenyl)-1-cyclohexyl-3-(4-arylpiperazin-1-yl)-2-phenylpropan-1-ols. Reduction of the prepared β-aminoketones with lithium aluminum hydride in absolute diethyl ether leads to the secondary aminopropanols. The prepared compounds could be converted into the corresponding dihydrochlorides.