Pyrimidine 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...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (49), p.8931-8935
Main Authors: Cavalli, Elfie S., Mies, Thomas, Rzepa, Henry S., White, Andrew J. P., Parsons, Philip J., Barrett, Anthony G.M.
Format: Article
Language:English
Subjects:
Dioxanes
Letter
Nucleosides
Pyrimidine Nucleosides
Uridine
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03152