title: Isoxazolidine-fused meso-tetraarylchlorins as key tools for the synthesis of mono- and bis-annulated chlorins.
abstract: 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.
authors.affiliation: UCIBIO/REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal. ana.silva@fc.up.pt.
authors.forename: António
authors.initials: A
authors.lastname: Aguiar
authors.forename: Andreia
authors.initials: A
authors.lastname: Leite
authors.forename: André M N
authors.initials: AM
authors.lastname: Silva
authors.forename: Augusto C
authors.initials: AC
authors.lastname: Tomé
authors.forename: Luís
authors.initials: L
authors.lastname: Cunha-Silva
authors.forename: Baltazar
authors.initials: B
authors.lastname: de Castro
authors.forename: Maria
authors.initials: M
authors.lastname: Rangel
authors.forename: Ana M G
authors.initials: AM
authors.lastname: Silva