1,3-Dipolar cycloaddition approach to isoxazole, isoxazoline and isoxazolidine analogues of C-nucleosides related to pseudouridine
2005; Elsevier BV; Volume: 62; Issue: 7 Linguagem: Inglês
10.1016/j.tet.2005.11.019
ISSN1464-5416
AutoresEvdoxia Coutouli‐Argyropoulou, P. S. LIANIS, Marigoula Mitakou, Anestis Giannoulis, Joanna Nowak‐Karnowska,
Tópico(s)Synthesis and Biological Evaluation
ResumoIsoxazole, isoxazoline and isoxazolidine analogues of C-nucleosides related to pseudouridine have been synthesized by 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrones derived from mono and disubstituted uracil-5-carbaldehydes and 2,4-dimethoxypyrimidine-5-carbaldehyde. The dimethoxy derivatives have been easily deprotected to the corresponding uracils bearing the heterocyclic ring instead of a sugar moiety. The regio and stereoselectivity of the reactions are discussed.
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