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Regioselective azotization or bis(amination) products of the title porphyrinoid were achieved in one-pot one-step syntheses under mild conditions using a selection of aromatic amines and isoamyl nitrite or p-chloranil, respectively. Structures, tautomery, chirality as well as spectroscopic and redox properties of the new systems were discussed.

Graphical abstract: Reactions of 2-aza-21-carbaporphyrin with aniline derivatives

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