Portal de Periódicos da CAPES

Artigo Produção Nacional Revisado por pares

BIBTEX RIS

Isoxazolidine-fused meso-tetraarylchlorins as key tools for the synthesis of mono- and bis-annulated chlorins

2015; Royal Society of Chemistry; Volume: 13; Issue: 26 Linguagem: Inglês

10.1039/c5ob00800j

1477-0539

António Aguiar, Andreia Leite, André M. N. Silva, Augusto C. Tomé, Luís Cunha‐Silva, Baltazar de Castro, Maria Rangel, Ana M. G. Silva,

Photosynthetic Processes and Mechanisms

The microwave-assisted catalytic hydrogenation of the isoxazolidine-fused meso-tetrakis(pentafluorophenyl)chlorin afforded directly a mono-annulated chlorin with a singular 1-methyl-2,3-dihydro-1H-benzo[b]azepine ring that resulted from the cleavage of the isoxazolidine N-O bond followed by an intramolecular nucleophilic aromatic substitution of an o-F atom. The subsequent treatment of the mono-annulated chlorin with NaH induced a second intramolecular nucleophilic aromatic substitution, generating a bis-annulated chlorin having an additional 2H-pyran ring.