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Kikelj, V., Julienne, K., Chalopin, T., Gouin, S. G., Evain, M. & Deniaud, D. (2015) Synthesis of Thiadiazolylaminoglycosides Through Ring Contraction of Triazinoglycosides Induced by [TBA-Ox]. J. Heterocycl. Chem. 52 1264–1268.
Added by: Laurent Cournède (2016-03-10 18:36:41) |
| Type de référence: Article DOI: 10.1002/jhet.2232 Numéro d'identification (ISBN etc.): 0022-152X Clé BibTeX: Kikelj2015 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: adenosine, amino nucleosides, biological evaluation, clitocine, efficient synthesis, inhibitors, inversa, oligodeoxynucleotides, pyrimidine, triazine derivatives Créateurs: Chalopin, Deniaud, Evain, Gouin, Julienne, Kikelj Collection: J. Heterocycl. Chem. |
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| Résumé |
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A new synthetic route to thiadiazolylaminoglycosides, by a ring expansion/ring contraction sequence of glycosyl triazines, has been developed. Two potential mechanisms of this oxidative ring contraction using [TBA-Ox] are discussed. The more plausible involves formation of an oxatriazepane intermediate followed by loss of formic acid, ring opening, and subsequent recyclization.
Added by: Laurent Cournède |