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ISSN 1998-9539

Synthesis and Properties of Tetrabenzoporphyrins with Fused N‑Octylmaleoimide Fragment

Nikolay E. Galanin,@ Leonid A. Yakubov, and Gennady P. Shaposhnikov


Ivanovo State University of Chemistry and Technology, Friedrich Engels Pr-t, 7, Ivanovo, 153000, Russia


@Corresponding author E-mail:


DOI: 10.6060/mhc2010.1.41
Macroheterocycles 2010 3(1) 41-47


The reaction of dipotassium salt of pyromellitic acid monoanhydride with hydrazine sulfate leads to 4,5-dicarboxyphthalylhydrazide (1,4-dioxo-1,2,3,4-tetrahydro-6,7-phthalazinedicarboxylic acid) 2, which upon treatment with 1-octylbromide produces a mixture of N,N- and N,O- alkylation products, 2,3-dioctyl-1,4-dioxo-1,2,3,4-tetrahydro- and 4-octyloxy-2-octyl-1-oxo-1,2-dihydro-6,7-phthalazinedicarboxylic acids (2 and 3). The acid 2 was converted to imide of 2,3-dioctyl-1,4-dioxo-1,2,3,4-tetrahydro-6,7-phthalazinedicarboxylic acid 4 which upon heating undegoes ring contraction with formation of N-octyldiimide of pyromellitic acid 5 and upon co-condensation with phthalimide and in the presence of zinc acetate gives the zinc complex of tetrabenzoporphyrin 6, containing N-octyldicarboimide moiety (fused N-octylmaleoimide fragment) in one of benzene rings. Demetallation of the zinc complex 6 upon reprecipitation from conc. sulfuric acid gives the free base porphyrin 7. Spectral properties of the new compounds have been studied.


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