Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions.

ABSTRACT: An efficient two-step procedure for the syntheses of pyrimidine nucleosides is presented. A series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared from β-anomeric isonitriles by reaction with Meldrum's acid or by allowing aminomethylene Meldrum's acid to react with an 1-aldofuranosyl halide or acetate. The resultant 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives underwent reaction with benzyl- or 2,4-dimethoxybenzyl isocyanate via transacylation to provide uridine-5-carboxylic acid derivatives and related nucleosides. These nucleoside carboxylic acids were converted into other C-5 derivatives by bromo-decarboxylation with N-bromosuccinimide.

SUBMITTER: Cavalli ES 

PROVIDER: S-EPMC9764413 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature