The 28-hetero-2,7-naphthiporphyrins reacted with triethylamine and diethylamine to form nonaromatic intracavity-extended macrocycles incorporating naphthodihydro-2H-pyran, naphthotetrahydropyridine, and naphthopyrrolotetrahydro-1H-azepine moieties. The new macrocycles were characterized in solution by means of NMR and UV-vis spectroscopy and in the solid state by XRD.