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Issue 26, 2015
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Isoxazolidine-fused meso-tetraarylchlorins as key tools for the synthesis of mono- and bis-annulated chlorins

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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.

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

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Article information


Submitted
22 Apr 2015
Accepted
20 May 2015
First published
20 May 2015

Org. Biomol. Chem., 2015,13, 7131-7135
Article type
Communication
Author version available

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

A. Aguiar, A. Leite, A. M. N. Silva, A. C. Tomé, L. Cunha-Silva, B. de Castro, M. Rangel and A. M. G. Silva, Org. Biomol. Chem., 2015, 13, 7131
DOI: 10.1039/C5OB00800J

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