One-Pot Sequential Knoevenagel-Aza-Annulation Strategy for the Synthesis of Peripherally Fused N-Aryl-2-pyridonoporphyrins.

Authors

Abhijeet Singh, Mahendra Nath

Published in

Organic letters. Aug 04, 2025. Epub Aug 04, 2025.

Abstract

One-pot sequential Knoevenagel-aza-annulation pathways allowed direct access to π-conjugated peripherally fused N-aryl-2-pyridonoporphyrins in appreciable yields. The unveiled cascade methodology involves a reaction between 2-formyl-meso-tetraarylporphyrins and 3-hydroxy-3-(2-hydroxyphenyl/1-hydroxynaphthalen-2-yl)-N-arylacrylamides, generated in situ by treating 4-hydroxycoumarin/4-hydroxy-2H-benzo[h]chromen-2-one with anilines in DMF at 150 °C to afford desired porphyrins within 4 h. The SCXRD analysis of porphyrin (4a) revealed a nonplanar structure with intramolecular π-π stacking and hydrogen bonding features. New porphyrins exhibited significantly red-shifted absorption and emission after a peripheral fusion.

PMID:
40758857
Bibliographic data and abstract were imported from PubMed on 05 Aug 2025.

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