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ISSN 1998-9539

A Study of the Reaction between Methylpyropheophorbide a and Hydrazine Hydrate

Ivan S. Lonin,a@ Evgeny S. Belyaev,a Aslan Yu. Tsivadze,a Gelii V. Ponomarev,b Natalya N. Lonina,c Andrew N. Fitch,d and Vladimir V. Chernysheva,e
Dedicated to Academician of Russian Academy of Sciences Aslan Yu. Tsivadze on the occasion of his Birthday
aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry of Russian Academy of Sciences, 119071 Moscow, Russia
bResearch Institute of Biomedical Chemistry, 119121 Moscow, Russia
cMoscow Technological University, Institute of Fine Chemical Technologies, 119571 Moscow, Russia
dEuropean Synchrotron Radiation Facility, B. P. 220, 38043 Grenoble Cedex, France
eChemical Department, Moscow State University, 119991 Moscow, Russia
@Corresponding author E-mail: loninis@gmail.com
 
DOI: 10.6060/mhc170832l
Macroheterocycles 2017 10(4-5) 474-479
 
The reaction between pyropheophorbide a methyl ester (1) and hydrazine hydrate has been studied. It was shown that the reagents ratio governs the particular reaction product formation. Treatment of 1 by excess of hydrazine hydrate (more than 3 eq.) yielded methylmesopyropheophorbide a hydrazone (2) as a major product. On the other hand, only methylmesopyropheophorbide a azine (4) was formed when the equimolar amounts of the reagents were applied. In order to prevent the C3-vinyl group reduction in 1 by hydrazine hydrate, the reaction was carried out in the presence of trifluoroacetic acid (TFA). It was shown, that the selectivity of the reaction is regulated by the hydrazine hydrate/TFA ratio. Thus, the optimal conditions for the selective synthesis of both methylpyropheophorbide a hydrazone (3) and azine (5) have been found. The formation of the dimeric structure of azines was determined by the X-ray powder diffraction.

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