N. S. Arutyunyan

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.

Synthesis and some transformations of 2-[2-isopropyl-4-(3-methylbutyl)tetrahydropyran-4-yl]-ethylamine

The condensation of 2-[2-isopropyl-4-(3-methylbutyl)tetrahydropyran-4-yl]ethylamine with aromatic aldehydes followed by reduction gave rise to secondary amines of tetrahydropyrane series. Reactions of the obtained amines with acetyl chloride, succinic and phthalic anhydrides resulted in the corresponding acetamides, succinimide, and phthalimide.

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 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 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 and some reactions of 2-[4-(2-chlorobenzyl)-6,6-dimethyltetrahydropyran-4-yl]ethylamine

Previously synthesized ethyl cyano(2,2-dimethyltetrahydropyran-4-ylidene)acetate I [3] reacts with 2chlorobenzylmagnesium chloride to form ethyl cyano[2,2-dimethyltetrahydropyran-4-yl-4-(2-chlorophenyl)]acetate II. The decarbethoxylation of the latter results in 3-(2-chlorobenzyl)-6,6-dimethyltetrahydropyran-3yl]acetonitrile III, the reduction of which with lithium aluminum hydride gives rise to 2-[4-(2-chlorobenzylDOI: 10.1134/S1070363213100289