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Carbaporphyrins and related systems replace one or more of the nitrogens of the porphyrin cavity with carbon atoms. Many examples of these systems are known, including benziporphyrins and naphthiporphyrins that incorporate benzene or naphthalene subunits, respectively. In this project, carbaporphyrinoids incorporating quinoline subunits (1) have been targeted for investigation. In these structures, a nitrogen has been reintroduced but placed at the periphery of the structure. A series of quinoline diesters 2 have been prepared and reduction with diisobutylaluminum hydride at -70 ºC afforded the related dialdehydes 3. In addition, a tripyrrolic intermediate 4 (tripyrrane) has been synthesized so that the new porphyrin analogues can be generated using a “3+1” methodology. Preliminary investigations into the formation of quiniporphyrin derivatives 1 are currently in progress.
Graybeal, Alexis, "Investigations into the Synthesis of 2,4-Quiniporphyrins" (2020). Chemistry. 1.