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ChemInform Abstract: Heterocyclic Nucleoside Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Dipoles.

✍ Scribed by D. R. ADAMS; A. S. F. BOYD; R. FERGUSON; D. S. GRIERSON; C. MONNERET

Publisher
John Wiley and Sons
Year
2010
Weight
37 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Heterocyclic Nucleoside Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Dipoles.

-The scope of the 1,3-dipolar cycloaddition reaction of nitrile oxides, nitronates and azides with 1-vinylthymine (I) is studied. Highly reactive 1,3-dipoles give the corresponding cycloadducts such as (III) and (XI), (XIII), (XIV) in good yields, whereas less reactive dipoles like nitrones and azides lead to unstable cycloadducts which eliminate thymine. Using allylthymine instead of compound (I) the mixture of the adducts (VI)-(VIII) is formed without any decomposition of the products. The reaction mechanisms are discussed. -(

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