2-Amino-3-cyano-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinolines (1) were synthesized by Michael addition of 1,3-cyclohexanedione with β,β-dicyanostyrene. The condensation of 2-amino-3-cyano-4- phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (1a) with 1,3-cyclohexanedione was carried out to give 2-(3-oxo-1-cyclohexenyl)amino-3-cyano-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (2a) which was converted into 1,3-dihy-dro-4-phenyl-5-amino-bis(2-oxo-cyclohexano)[b,g]-1,8-naphthridine (3a). 5,6,7,8,9,10- Hexahydro-9-aryl-benzo[c]acridin-5-one (4) was obtained using one pot method by co-refluxing of aromatic aldehyde, α-naphthylamine and 1,3-cyclohexanedione. The mechanism of the related reactions was tentatively discussed and the structures of new compounds 1a～4c were characterized by elemental analysis, IR and ¹H NMR spectra.

Key words: quinoline, naphthyridine, nitrogenated heterocyclic compound, acridine, cyclization reaction