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

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 we...

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Bibliographic Details
Published in:Monatshefte für Chemie 2010-04, Vol.141 (4), p.451-459
Main Authors: Jachak, Madhukar N., Birari, Dilip R., Toche, Raghunath B., Ghagare, Maruti G., Bagul, Sandeep M.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary: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 1 -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. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-010-0280-x