Cycloaddition reaction on 3-vinylemeraldins: formation of unexpected porphyrins with seven-membered exocyclic ring systems

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Reaction of 3-vinylemeraldin with dimethyl acetylenedicarboxylate (DMAD) produced a benzoporphyrin derivative via [4+2] Diels-Alder adduct and an unexpected porphyrin containing a seven-membered ring system (yield 15%) fused at the 3- and 5-positions of the macrocycle. The benzoporphyrin derivatives containing N-alkylated fused imide ring system exhibit long wavelength absorptions near λ max 725 nm. In preliminary in vivo screening some of these analogs were found to be more effective than the related protoporphyrin IX (PP-IX) based benzoporphyrin derivative (BPDMA).