BASE-PROMOTED REACTION OF O-SULFONYLATED HYDROXAMIC ACIDS WITH NUCLEOPHILES - A NEW METHOD FOR THE SYNTHESIS OF ALPHA-SUBSTITUTED AMIDES

被引：28

作者：

HOFFMAN, RV

NAYYAR, NK

CHEN, WT

机构：

[1] Department of Chemistry, New Mexico State University, Las Cruces

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 21期

关键词：

D O I：

10.1021/jo00047a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

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页码：5700 / 5707

页数：8

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