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Effect of C-5 substituent on the regioselectivity of N-ferrocenoylation of uracil

Nucleosides and their analogs have a significant role in drug discovery and development due to their remarkable chemotherapeutic activities. In this regard, the extensive endeavors have been performed so far to synthesize the various structurally diverse nucleosides. The presence of multiple nucleophilic sites in nucleobases with comparable reactivity, traditionally affords a complex mixture of products through in reactions with low regioselectivity [1]. Also it has been found that the position of N-acylation depends on the reaction temperature, base catalyst, and acylation agent employed [2]. Our research group have developed a one-step synthetic route to prepare ferocenoyl derivatives of nucleobases, the Fc–C=O fragment has been linked to “standard” pyrimidine bases. In aforementioned reactions the bases have been ferrocenoylated selectively at N1- position of the pyrimidine ring [3]. Consequently, here we will focus on examining the effect of the substituent at position C-5 uracil and various deprotonating agents (NaH, Et3N) and solvents (DMF, CH3CN) on the regioselectivity of N- ferrocenoylation of the nucleobase (Fig 1). The position of substitution in products and their proportion will be confirmed by NMR-spectroscopy.

ferocene ; C5-derivatives of uracil ; N1 and/or N1/N3-conjugates

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