Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions

Org Lett. 2022 Dec 16;24(49):8931-8935. doi: 10.1021/acs.orglett.2c03152. Epub 2022 Nov 4.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dioxanes*
  • Nucleosides
  • Pyrimidine Nucleosides*
  • Uridine

Substances

  • Dioxanes
  • Pyrimidine Nucleosides
  • Uridine
  • Nucleosides