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Synthesis of uracil derivatives and their alkylation: an approach to peptide non-nucleic acid monomers

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Abstract

N3-substituted 5-acetyluracils derived from corresponding N3-substituted 5-acetylcytosines are versatile functional precursors that allow the introduction of various aliphatic, aromatic, carbocyclic, and carbamoyl functionalities at N1-position. A series of 1,3-disubstituted 5-acetyluracils were synthesized by alkylation at N1-position. For the introduction of carbamoyl functionalities a convergent approach is studied, leading to N-arylacetamide derivatives; the linear approach furnished peptide non-nucleic acid monomers by replacement of active ester with amino acid esters in good yields.

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Acknowledgments

The authors gratefully acknowledge financial support of this project by UGC, New Delhi, India. Also we thanks Principal, K.T.H.M. College, Nashik, 422 002 for facilities.

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Authors and Affiliations

  1. Department of Chemistry, Organic Chemistry Research Center, K.T.H.M. College, Gangapur Road, Nashik, 422 002, Maharashtra, India

    Madhukar N. Jachak, Dilip R. Birari, Raghunath B. Toche, Maruti G. Ghagare & Sandeep M. Bagul

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  1. Madhukar N. Jachak
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  2. Dilip R. Birari
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  3. Raghunath B. Toche
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  4. Maruti G. Ghagare
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  5. Sandeep M. Bagul
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Correspondence to Madhukar N. Jachak.

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Jachak, M.N., Birari, D.R., Toche, R.B. et al. Synthesis of uracil derivatives and their alkylation: an approach to peptide non-nucleic acid monomers. Monatsh Chem 141, 451–459 (2010). https://doi.org/10.1007/s00706-010-0280-x

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  • DOI: https://doi.org/10.1007/s00706-010-0280-x

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