The selective N-4 alkylation of cytosine plays a critical role in the synthesis of biologically active molecules. This work focuses on the development of practical reaction conditions toward a regioselective synthesis of N-4-alkyl cytosine derivatives. The sequence includes a direct and selective sulfonylation at the N-1 site of the cytosine, followed by the alkylation of the amino site using KHMDS in CH2Cl2/THF mixture, providing a fast and efficient approach consistent with pyrimidine-based drug design.
N-4 Alkyl cytosine derivatives synthesis: a new approach / De Nisco, Mauro; Di Maio, Antonio; Manfra, Michele; Ostacolo, Carmine; Bertamino, Alessia; Campiglia, Pietro; Gomez-Monterrey, Isabel M.; Pedatella, Silvana. - In: REACTIONS. - ISSN 2624-781X. - 3:1(2022), pp. 192-202. [10.3390/reactions3010014]
N-4 Alkyl cytosine derivatives synthesis: a new approach
Carmine OstacoloFormal Analysis
;Isabel M. Gomez-Monterrey
Penultimo
Funding Acquisition
;Silvana Pedatella
Ultimo
Writing – Review & Editing
2022
Abstract
The selective N-4 alkylation of cytosine plays a critical role in the synthesis of biologically active molecules. This work focuses on the development of practical reaction conditions toward a regioselective synthesis of N-4-alkyl cytosine derivatives. The sequence includes a direct and selective sulfonylation at the N-1 site of the cytosine, followed by the alkylation of the amino site using KHMDS in CH2Cl2/THF mixture, providing a fast and efficient approach consistent with pyrimidine-based drug design.| File | Dimensione | Formato | |
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