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Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides

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Abstract

Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-alkylation reaction with primary or secondary alcohols using TsCl/TEA/K2CO3 in bmim[Br] to afford the products in good-to-excellent yields. The influence of factors in this method including the type of ionic liquid, base and sulfonating agents was discussed. The current method showed an appropriate selectivity in reaction with primary alcohols in comparison with secondary alcohols. This protocol is mild, safe and easy to apply; moreover, it is quite compatible with eco-friendly and green chemistry protocols, since the exploitation of toxic and hazardous materials such as DMF and alkyl halides has been prevented.

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Acknowledgments

We are grateful to Shiraz University of Technology Research Council for partial support of this work.

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Authors and Affiliations

  1. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology, 71555-313, Shiraz, Iran

    Mohammad Navid Soltani Rad, Somayeh Behrouz & Narjes Kaviani

  2. Department of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran

    Elham Zarenezhad

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  1. Mohammad Navid Soltani Rad
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  2. Somayeh Behrouz
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  3. Elham Zarenezhad
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Correspondence to Mohammad Navid Soltani Rad or Somayeh Behrouz.

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More experimental details including characterization data, 1H NMR and 13C NMR for all new and known compounds are available online.

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Rad, M.N.S., Behrouz, S., Zarenezhad, E. et al. Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides. J IRAN CHEM SOC 12, 1603–1612 (2015). https://doi.org/10.1007/s13738-015-0633-9

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