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Communication | Regular issue | Vol 68, No. 5, 2006, pp.885-888
Published online, 31st March, 2006
DOI: 10.3987/COM-06-10691
■ Synthesis of Isoxazoline-fused Chlorins by 1,3-Dipolar Cycloaddition Reaction of Porphyrins with Alkyl Nitrile Oxides

Stanislaw Ostrowski,* Przemyslaw Wyrebek, and Agnieszka Mikus

*Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland

Abstract

meso-Tetraphenylporphyrin and its β-nitro zinc complex derivative react at higher temperature with unstable alkyl nitrile oxides affording isoxazoline-fused chlorins according to dipolar [3+2]-cycloaddition pathway. The respective nitrile oxides were in situ generated from the corresponding nitroalkanes in the presence of triethylamine and phenyl isocyanate. The products obtained are attractive intermediates for further functionalization of porphyrins and may be of potential use as sensitizers in photodynamic therapy.