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

David R. Adams, A. S F Boyd, R. Ferguson, David S. Grierson, Claude Monneret

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

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has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle.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

Original languageEnglish
Pages (from-to)1053-1075
Number of pages23
JournalNucleosides and Nucleotides
Volume17
Issue number6
Publication statusPublished - 1998

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