Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions

被引：3

作者：

Cavalli, Elfie S. ^{[1
]}

Mies, Thomas ^{[1
]}

Rzepa, Henry S. ^{[1
]}

White, Andrew J. P. ^{[1
]}

Parsons, Philip J. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, Mol Sci Res Hub, White City Campus, London W12 0BZ, England

来源：

ORGANIC LETTERS | 2022年

关键词：

ISOCYANIDES; DERIVATIVES; ACID;

D O I：

10.1021/acs.orglett.2c03152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-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.

引用

页码：8931 / 8935

页数：5

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