A Study of the Reaction between Methylpyropheophorbide a and Hydrazine Hydrateстатья
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Аннотация: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.