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Ferrocenoyl-adenine conjugate: Regioselectivity of the acylation reaction

The interest in ferrocene-modified purine and pyrimidine derivatives during the last two decades was motivated by the unique properties displayed by ferrocene, in particular its redox ability, membrane permeability and low toxicity. In ferrocenyl-nucleobases, the iron-containing ferrocenyl moiety mimics the ribose fragment of nucleosides [1]. Our research group has developed a one-step synthetic route to prepare ferocenoyl derivatives of nucleobases, the Fc–C=O fragment has been linked to “standard” pyrimidine bases. The ferrocenoyl units introduced into different N-positions of the pyrimidine ring systems and the regioselective of substitution in products has been confirmed by NMR spectroscopic analysis and quantum chemical calculations [2]. In continuation of our research on ferrocenyl-nucleobases with carbonyl groups as a linker, ferrocenoyl-adenine conjugate were synthesized. Most of the reactions result in the formation of a mixture of N7- and N9-substituted products (Fig. 1). The ratio of these isomers depends on reaction conditions (solvents, temperature of deprotection and coupling reaction, base catalyst). The position of substitution in products and the reaction regioselectivity will be explored by spectroscopy methods (1D and 2D-NMR, FTIR) and quantum chemical calculations (DFT level of theory).

chemistry, electrochemistry, synthesis' reaction mechanism, DFT

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