Synthesis, structure, and biological activity of [2.2]paracyclophanes. 7. Synthesis of 2-([2.2]paracyclophan-4-yl)pyridines, -tetrahydroquinolines, and -benzo[h]quinolines based on condensation of 4-(β-dimethylaminopropionyl)[2.2]paracyclophane with primary amines

Condensation of 4-(β-dimethylaminopropionyl)paracyclophane with aliphatic aldehydes or cyclohexanones in the presence of hydroxylamine gave 2-([2.2]paracyclophan-4-yl)pyridines and -5,6,7,8-tetrahydroquinolines respectively. Reaction of these salts with α-naphthylamine gives a mixture of paracyclophanyl substituted 1,2,3,4-tetrahydrobeno[h]quinoline and benzo[h]quinoline. ©1998 Plenum Publishing Corporation