Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of β-Octaethylporphyrin and Coproporphyrin I Tetraethyl Ester

Alena O. Shkirdova,^a,b Ilya A. Zamilatskov,^a@ Nadezhda M. Stanetskaya,^a Victor A. Tafeenko,^c Vladimir S. Tyurin,^a Vladimir V. Chernyshev,^a,c Gelii V. Ponomarev,^d and Aslan Yu. Tsivadze^a

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, 119071 Moscow, Russian Federation

^bMoscow Technological University, Institute of Fine Chemical Technologies, 119571 Moscow, Russian Federation

^cChemical Department, Moscow State University, 119899 Moscow, Russian Federation

^dResearch Institute of Biomedical Chemistry, 119121 Moscow, Russian Federation

^@Corresponding author E-mail: joz@mail.ru

DOI: 10.6060/mhc171148z

Macroheterocycles 2017 10(4-5) 480-486

N-substituted hydrazones of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I were obtained. These compounds can serve as intermediate compounds for the preparation of meso-functionalized derivatives of porphyrins by means of various reactions. In the first stage Vilsmeier-Haack reaction was carried out by the interaction of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I with N,N-dimethylformamide and phosphorus(V) oxochloride forming the so-called “phosphorus complex”, which was hydrolyzed with saturated solution of sodium acetate. The corresponding meso-formyl derivatives of metal porphyrins were obtained as a result. Synthesis of the hydrazones was carried out by the reactions of meso-formyl derivatives with the hydrazines using trifluoroacetic acid as a catalyst. The result of the reaction was formation of hydrazones in the form of a mixture of E- and Z-isomers, which were separated using preparative thin layer chromatography. Thus a series of hydrazones with different substituents at the nitrogen atom was obtained. The structures of all obtained compounds were determined using the methods of NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. For nickel complex of tosylhydrazone derivative of β-octaethylporphyrin the crystal structure was determined using X-ray diffraction. X-ray analysis shows that porphyrin molecules in the crystal form dimers bonded by two hydrogen bonds between the hydrogen atom of the NH-group of hydrazone and the oxygen atom of the sulfonate groups.

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Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of β-Octaethylporphyrin and Coproporphyrin I Tetraethyl Ester

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