Heterocyclic nucleoside analogues by cycloaddition reactions of 1-vinylthymine with 1,3-dipoles

1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive...

Full description

Saved in:
Bibliographic Details
Published in:Nucleosides & nucleotides 1998-06, Vol.17 (6), p.1053-1075
Main Authors: Adams, D R, Boyd, A S, Ferguson, R, Grierson, D S, Monneret, C
Format: Article
Language:English
Subjects:
Heterocyclic Compounds - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleosides - chemistry
Thymine - analogs & derivatives
Thymine - chemistry
Vinyl Compounds - chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1-(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.
ISSN:0732-8311
DOI:10.1080/07328319808004220