Synthesis and Analgesic Activity of N,6-Diaryl-4-hydroxy-4-methyl-2-oxocyclohexane-1-carboxamides and Their Dehydration Products

A series of new N,6-diaryl-4-hydroxy-4-methyl-2-oxocyclohexane-1-carboxamides was obtained through the reaction of N-arylamides of acetoacetic acid with benzalacetone and 4-chlorobenzalacetone under basic conditions (KOH) in methanol at room temperature. Increasing of the amount of potassium hydroxide used in the reaction led to the formation of dehydration products, namely N,6-diaryl-4-methyl-2-oxocyclohex-3-ene-1-carboxamides. The latter were also formed by using unsubstituted acetoacetamide and N-methylacetoacetamide. The synthesized compounds were tested for analgesic activity.