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

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Antnio Aguiar (Author) Other; Andreia Leite (Author) Other; Andre M N Silva (Author) Other; Augusto C Tome (Author) Other; Luis Cunha Silva (Author) Other; Baltazar de Castro (Author) FCUP; Maria Rangel (Author) ICBAS; Ana M G Silva (Author) Other

Journal

Title: Organic and Biomolecular Chemistry

Vol. 13

Pages: 7131-7135

ISSN: 1477-0520

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 24 Citations

Scopus - 26 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-00G-CGC

DOI: 10.1039/c5ob00800j

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 5