Synthesis and Structure Elucidation of β,β,β-Trinitro-meso-tetraphenylporphyrin Derivatives
Аннотация
The preparation, chromatographic isolation, and structure elucidation of β,β,β-substituted isomers of trinitro-5,10,15,20-tetraphenylporphyrin complexes are described. meso-Tetraphenylporphyrin (m-TPP) chelates (CuII and ZnII) in the reaction with nitric acid (yellow fuming HNO3, d = 1.52) in CHCl3 resulted in the formation of a mixture of nitroderivatives with combined yields of ca 50%. This nitration (under optimized conditions: 1–2 min, r.t.) can be carried out selectively to give mainly β,β,β-trinitro-compounds in the yield of up to 30-40%. From the above mixtures of seven possible regioisomers to form, two or three of them were usually isolated for which the structures were assigned on the basis of 1H NMR spectra including HSQC and HMBC measurements. These types of products are attractive starting materials for synthesis of potential anticancer PDT agents of unique structure that are practically not available by any other alternative method
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