The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole

The double bond in 4,7-dihydroisoindole derivatives was shown to be a useful reaction site to afford new porphyrinogenic pyrrolic precursors bearing substituted annelated rings via various addition reactions. These precursors are further used to afford new extended porphyrins substituted in the annelated rings. The Sharpless osmium-catalyzed dihydroxylation of dihydroisoindole system was shown to be useful in the synthesis of non-ionogenic water-soluble porphyrin, as well as tetrabenzoporphyrin bearing acetoxy-substituents in benzo-rings. The reverse electron-demand Diels–Alder reaction with tetrachlorothiophene-1,1-dioxide afforded new polychlorosubstituted tetranaphthoporphyrin.