Abstract

ALONSO, Cristina M. A. et al. Reaction of 2-Amino-5,10,15,20-Tetraphenylporphyrinatonickel(II) with α,ß-Unsaturated Acyl Chlorides: Synthesis of 2-pyridone-fused Porphyrin Derivatives. J. Mex. Chem. Soc [online]. 2006, vol.50, n.3, pp.100-105. ISSN 1870-249X.

The reactivity of 2-amino-5,10,15,20-tetraphenylporphyrinatonickel(II) with acryloyl and cinnamoyl chlorides was studied. The reaction with acryloyl chloride afforded the dihydro-2-pyridone fused porphyrin 3a resulting from an aza-annulation reaction. The oxidation of 3a afforded the corresponding 2-pyridone derivative. N-Acylation reaction is an important competing transformation, giving rise to amide derivatives. The structures of the novel compounds were established by NMR and mass spectrometry studies.

Keywords : Porphyrins; aza-annulation reactions; 2-pyridones; acyl chlorides.

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