Abstract
New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl)pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity.
Highlights
The use of solid materials as reusable catalysts in chemical synthesis contributes significantly to simplify diverse processes like separation, purification and isolation of the reaction products, to optimize the conversion and performance, as well as to decrease pollutants generation
Azanucleosides are analogues of nucleosides with ribofuranosyl moieties, where the oxygen is replaced by a nitrogen atom (Figure 1b), which allows inhibiting the hydrolysis of the glycosidic bond by glycohydrolases [29,30,31,32]
We have demonstrated that sulphated zirconia is an efficient catalyst in the regioselective nucleophilic opening of the oxiranes 1-allyl-3-(oxiran-2ylmethyl) pyrimidine-2,4-(1H,3H)-dione (6a) and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl) pyrimidine-2,4-(1H,3H)-dione (6b) with (S)-prolinol to give the azanucleosides 8a and 8b with good yield
Summary
The use of solid materials as reusable catalysts in chemical synthesis contributes significantly to simplify diverse processes like separation, purification and isolation of the reaction products, to optimize the conversion and performance, as well as to decrease pollutants generation. Azanucleosides are analogues of nucleosides with ribofuranosyl moieties, where the oxygen is replaced by a nitrogen atom (Figure 1b), which allows inhibiting the hydrolysis of the glycosidic bond by glycohydrolases [29,30,31,32]. With this background, we considered the possibility to insert a pyrrolidine ring and hydroxymethyl group in the position N-3 of pyrimidinedione aiming to generate a new kind of nucleosides analogues (Figure 1c). In the present paper we describe a new protocol of the azanucleosides synthesis by nucleophilic opening of epoxides using sulphated zirconia as catalyst
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