biostudies-literatureCavalli ESLeverhulme TrustGlaxoSmithKline8931-8935https://www.ebi.ac.uk/biostudies/studies/S-EPMC9764413biostudies-literatureUnknown24(49)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 <i>N</i>-bromosuccinimide.Organic lettersPyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions.PMC9764413RPG-2020-273Mies TCavalli ESRzepa HSParsons PJWhite AJPBarrett AGMfalsePyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions.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 <i>N</i>-bromosuccinimide.2022-01-01T00:00:00Z2022 Dec2025-04-26T09:49:13.583Z2025-04-06T13:08:24.892ZS-EPMC97644133633152910.1021/acs.orglett.2c03152