An effective synthesis of hybrid systems has been carried out, including a biogenic pyridone fragment and linearly bound (het)aryl substituents, by O,N-recycling of substituted aminochromencarbonitriles under the action of iodine. The composition and structure of the newly obtained 2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitriles have been determined using elemental analysis and spectral methods. Possible reaction patterns are presented and discussed.