Synthesis of pyranosyl amidoximes by addition of amines to pyranosyl nitrile oxides

Kenneth W.J. Baker, Katherine S. Horner, Stephen A. Moggach, R. Michael Paton, Iain A.S. Smellie

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Abstract

Addition of amines to pyranosyl nitrile oxides, generated by base-induced dehydrochlorination of the corresponding hydroximoyl chloride, affords pyranosyl N-alkyl/aryl-formamide oximes (41-90%). Reaction with amino acid esters yields the corresponding amidoximes and/or 3-pyranosyl-1,2,4-oxadiazin-6-ones. The structure of N-phenyl-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)formamide oxime was established by X-ray crystallography.

Original languageEnglish
Pages (from-to)8913-8916
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number48
DOIs
Publication statusPublished - 22 Nov 2004

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