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

被引：15

作者：

Baker, KWJ ^{[1
]}

Horner, KS ^{[1
]}

Moggach, SA ^{[1
]}

Paton, RM ^{[1
]}

Smellie, IAS ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

C-glycosides; nitrile oxides; amidoximes; 1,2,4-oxadiazin-6-ones;

D O I：

10.1016/j.tetlet.2004.09.173

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-beta-D-xylopyranosyl)formamide oxime was established by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8913 / 8916

页数：4

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