Isomers of β ,β -Dinitro-5,10,15,20-tetraphenylporphy-rin Derivatives: Valuable Starting Materials for Further Transformations

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Agnieszka MikusStanisław Ostrowski

Abstract

The synthesis, chromatographic isolation, and structure elucidation of β,β-substituted isomers of dinitro-5,10,15,20-tetraphenylporphyrin complexes are described. meso-Tetraphenyl-porphyrin chelates (CuII, NiII, CoII) upon reaction wit e.g., itric acid (yellow HNO₃, d = 1.52, diluted to 25⁻50%) in CHCl₃ formed a mixture of nitro-derivatives with combined yields of ca 80%. This nitration (under optimized conditions: 25⁻30% HNO₃, 30⁻40 min, r.t.) can be carried out selectively to give mainly β,β-dinitro-compounds in yields of up to 73%. From the above mixtures of five possible regioisomers that can be formed, usually two or three of them were isolated, for which the structures were assigned on the basis of ¹H NMR spectra including COSY and NOESY measure-ments. These types of products are attractive starting materials for synthesis of potential anticancer PDT agents with unique structures, being practically unavailable by any other alternative method.

References

Oct 24, 2001·The Journal of Organic Chemistry·Kalyn M. SheaKevin M. Smith
Aug 9, 2016·Chemical Reviews·Masahiko Taniguchi, Jonathan S Lindsey

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Citations

Jan 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nuno M M MouraMaria Graça P M S Neves
May 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yoshiki SasakiHidemitsu Uno
Oct 30, 2020·Chemistry, an Asian Journal·Agnieszka Mikus, Beata Łopuszyńska

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Methods Mentioned

BETA
column chromatography
NMR

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