N-Vinyl-Nitroimidazole Cycloadditions: Potential Routes to Nucleoside Analogues

Russell Clayton; Christopher A. Ramsden

doi:10.1055/s-2005-872083

PAPER

N-Vinyl-Nitroimidazole Cycloadditions: Potential Routes to Nucleoside Analogues

Russell Clayton, Christopher A. Ramsden*
Lennard-Jones Laboratories, School of Chemistry and Physics, Keele University, Keele, Staffordshire ST5 5BG, UK
Fax: +44(1782)712378; e-Mail: c.a.ramsden@chem.keele.ac.uk;

Abstract

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Abstract

Cycloaddition reactions of 4-nitro- and 5-nitro-1-vinylimidazoles have been investigated. The cycloadducts obtained are potential intermediates for synthesis of purine nucleoside analogues via reduction to the corresponding aminoimidazoles. A byproduct obtained using benzonitrile oxide as 1,3-dipolarophile has been identified as a novel tricyclic isomer 12 of the cycloadduct 11.

Key word

nitroimidazole - vinylimidazole - 1,3-dipolar cycloadditions - isoxazoline - nucleoside analogues

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References

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