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.