Porphyrin-2,3-dione mono- and dioximes were used as starting materials for the efficient syntheses of mono- and bis-quinoline-annulated porphyrins and their corresponding N-oxides. Owing to an extended π-system, these novel porphyrinoid chromophores show significantly red-shifted UV-vis spectra compared to the parent porphyrins. A crystal structure exemplifies the nonplanar conformation of the macrocycle.