Pyrimidine nucleosides syntheses by late-stage base heterocyclization reactions
File(s)
Published version
Author(s)
Type
Journal Article
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.
Date Issued
2022-12-16
Date Acceptance
2022-11-01
Citation
Organic Letters, 2022, 24 (49), pp.8931-8935
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
8931
End Page
8935
Journal / Book Title
Organic Letters
Volume
24
Issue
49
Copyright Statement
© 2022 American Chemical Society. This work is licensed under a CC BY licence.
License URL
Identifier
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000883003000001&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
ISOCYANIDES
DERIVATIVES
ACID
Publication Status
Published
Date Publish Online
2022-11-04