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

Article abstract of DOI:10.1080/07328319808004220

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has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle.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.

Full text of DOI:10.1080/07328319808004220

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Nucleosides and Nucleotides
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Heterocyclic Nucleosede Analogues
by Cycloaddition Reactions of 1-
Vinylthymine with 1,3-Depoles
David R. Adams a , Alan S. F. Boyd a , R. Ferguson a , David S.
Grierson b & Claude Monneret c
a Chemistry Department, Heriot-Watt University, Riccarton,
Edinburgh, EH14 4AS, UK
b Institut de Chimie des Substances Naturelles CNRS, Ave de la
Terrasse, 91198, Gif-sur-Yvette, France
c Service de Chimie, CNRS, URA 1387, Institut Curie, Section de
Biologic, 26 rue d'Ulm, Paris Cedex, 05, France
Version of record first published: 21 Aug 2006.
To cite this article: David R. Adams , Alan S. F. Boyd , R. Ferguson , David S. Grierson & Claude
Monneret (1998): Heterocyclic Nucleosede Analogues by Cycloaddition Reactions of 1-Vinylthymine
with 1,3-Depoles, Nucleosides and Nucleotides, 17:6, 1053-1075
To link to this article: http://dx.doi.org/10.1080/07328319808004220
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