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

摘要

N~3-substituted 5-acetyluracils derived from corresponding N~3-substituted 5-acetylcytosines are versatile functional precursors that allow the introduction of various aliphatic, aromatic, carbocyclic, and carbamoyl functionalities at N~1-position. A series of 1,3-disubstituted 5-acetyluracils were synthesized by alkylation at N'-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.