Reaction of 2-Amino-5,10,15,20-Tetraphenylporphyrinatonickel(II) with α,β-Unsaturated Acyl Chlorides: Synthesis of 2-pyridone-fused Porphyrin Derivatives

Authors

  • Cristina M. A. Alonso University of Aveiro
  • Maria G. P. M. S. Neves University of Aveiro
  • Augusto C. Tomé University of Aveiro
  • Artur M. S. Silva University of Aveiro
  • José A. S. Calveiro University of Aveiro

Keywords:

Porphyrins, aza-annulation reactions, 2-pyridones, acylchlorides

Abstract

Abstract. 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. NAcylation 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.

Resumen. En el presente trabajo se estudió la reactividad de 2-amino-5,10,15,20-tetrafenilporfirinatoníquel(II) con los cloruros de acriloílo y cinamoílo. De la reacción de aza-anulación con cloruro de acriloílo resultó la porfirina 3a que posee un anillo de dihidro-2-piridona fundido. La oxidación de 3a permitió la obtención del derivado de 2-piridona correspondiente. La reacción de N-acilación es una importante transformación competitiva, que origina los derivados de amida. La estructura de los nuevos compuestos fue establecida por estudios de RMN y por Espectrometría de Masa.

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Author Biographies

Cristina M. A. Alonso, University of Aveiro

Department of Chemistry

Maria G. P. M. S. Neves, University of Aveiro

Department of Chemistry

Augusto C. Tomé, University of Aveiro

Department of Chemistry

Artur M. S. Silva, University of Aveiro

Department of Chemistry

José A. S. Calveiro, University of Aveiro

Department of Chemistry

References

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Published

2020-08-07

Issue

Vol. 50 No. 3 (2006): Special issue of the J. Mex. Chem. Soc. includes scientific articles dedicated to Professor Pedro Joseph Nathan

Section

Regular Articles

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