Synthesis and Antibacterial Activity of Oxalates and Acetamides of {2-[2-Sopropyltetrahydropyran-4-yl-4-(4-Fluorophenyl)]Ethyl}Arylamines

The reaction of cyano(2-isopropyltetrahydropyran-4-ylidene)acetic acid ethyl ester and 4-fluorophenylmagnesium bromide produced the cyanoester that was decarboxylated to the corresponding nitrile. Reduction of the latter by LiAlH 4 formed 2-[4-(4-fluorophenyl)-2-isopropyltetrahydropyran-4-yl]ethylamine, reaction of which with aromatic aldehydes synthesized azomethines that were then reduced by NaBH 4 to secondary amines. The last were transformed to oxalates and acetamides. It was shown that the secondary amine oxalates possessed high antibacterial activity.