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Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases

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Abstract

Novel analogues of nucleosides tethered on a chiral pyrrolidin-2-one were prepared, but the imide functionality was unstable under basic conditions. Thus, the carbonyl group was removed from pyrrolidin-2-one, and nucleoside analogues bearing a pyrrolidine ring were synthesized, which were unaffected under basic conditions. A nucleoside dimer was also obtained, bearing a carbamate linkage between two units.

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Acknowledgments

We thank Nanodream, s.r.l. (Jesi, Ancona, Italy) for financial support and use of Varian MR-400 NMR spectrometer.

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Authors and Affiliations

  1. Di.S.V.A. – Chemistry, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy

    Gianluca Martelli, Antonella Monsignori, Mario Orena & Samuele Rinaldi

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  1. Gianluca Martelli
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  2. Antonella Monsignori
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  3. Mario Orena
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  4. Samuele Rinaldi
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Correspondence to Samuele Rinaldi.

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Martelli, G., Monsignori, A., Orena, M. et al. Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases. Monatsh Chem 145, 1357–1364 (2014). https://doi.org/10.1007/s00706-014-1251-4

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  • DOI: https://doi.org/10.1007/s00706-014-1251-4

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