Issue 39, 2013

6-Oxopyriphlorins

Abstract

Reaction of 2,6-pyridinedicarbaldehyde with a series of tripyrranes in the presence of trifluoroacetic acid, followed by oxidation of a pyriphlorin intermediate with silver(I) acetate, gave 6-oxopyriphlorins in moderate to good yields. The oxophlorin analogues were nonaromatic porphyrinoids that gave bright green colored solutions. Protonation with TFA afforded species that were attributed to mono- and dicationic structures. The proton NMR spectra in TFA–CDCl3 showed downfield shifts to the meso-protons and upfield shifts to the interior NH resonances that indicated the presence of a weakly diatropic dicationic species. Reaction of a 6-oxopyriphlorin with nickel(II) acetate in DMF or palladium(II) acetate in acetonitrile afforded the corresponding metallo-derivatives.

Graphical abstract: 6-Oxopyriphlorins

Supplementary files

Article information

Article type
Paper
Submitted
22 Jul 2013
Accepted
03 Sep 2013
First published
03 Sep 2013

Org. Biomol. Chem., 2013,11, 6841-6848

6-Oxopyriphlorins

A. M. Young and T. D. Lash, Org. Biomol. Chem., 2013, 11, 6841 DOI: 10.1039/C3OB41506F

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