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ISSN 1998-9539

Synthesis of β-Octaethylporphyrin Conjugates with Nitrogen and Sulfur Containing Heterocycles

Alena O. Shkirdova,a Ekaterina A. Orlova,a Gelii V. Ponomarev,b Vladimir S. Tyurin,a Ilya A. Zamilatskov,a@ and Aleksey K. Buryaka 
aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russia
bV.N. Orekhovich Institute of Biomedical Chemistry, 119121 Moscow, Russian Federation
@Corresponding author E-mail: joz@mail.ru
 
DOI: 10.6060/mhc211046z
Macroheterocycles 2021 14(3) 204-208
 
Сonjugates of Ni(II) b-octaethylporphyrin with nitrogen and sulfur containing heterocycles were obtained by meso-functionalization of the porphyrin. The meso-functionalization of Ni(II) b-octaethylporphyrin was performed by the Vilsmeier-Haack formylation reaction, followed by the Knoevenagel reaction of Ni(II) meso-formyl- b-octaethylporphyrin with CH-acids: malonic ester, thiohydantoin, and thiobarbituric acid. The product of condensation of the porphyrin with malonic ester was cyclized with hydrazine to the corresponding porphyrin conjugate with pyrazolidine-3,5-dione. The optical spectra of the obtained new dyes are modified compared to that of the initial compounds. The spectral changes of the porphyrin conjugate with thiobarbituric acid are particularly dramatic reflecting the considerable interaction between tetrapyrrolic and heterocyclic chromophores in the molecule.

 

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