Amino substituted 1, 2, 3, 4-tetrahydronaphthalene and 5, 6, 7, 8-tetrahydroquinoline derivatives (1, 2, 3, 4-tetrahydro-6-methoxy-N-methyl-2-phenyl-2-naphthylamine, 1, 2, 3, 4-tetrahydro-6-methoxy-N, N-dimethyl-2-phenyl-2-naphthylamine, 5, 6, 7, 8-tetrahydro-6-(methylamino)-6-phenylquinoline and 5, 6, 7, 8-tetrahydro-6-(dimethylamino)-6-phenylquinoline) were synthesized. Thus, Michael adducts of methyl vinyl ketone and acrylonitrile to methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate (I) were used for formation of skeleton of naphthalene and quinoline, respectively. Quinoline derivative was also obtained by condensation of cyclohexanone derivative with 3-aminoacrolein. Amino function was derived from nitrile via Hofmann reaction of amide. Furthermore, an interesting tricyclic compound, 3, 8a-ethano-3, 4, 4a, 8a, 5, 6-hexahydro-3-phenyl-2, 7 (1H, 8H)-quinolinedione, was obtained on cyclization reaction of a Michael adduct (IIa).
