Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of. alpha.-substituted amides

RV Hoffman, NK Nayyar, W Chen

Index: Hoffman, Ribert V.; Nayyar, Naresh K.; Chen, Wenting Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5700 - 5707

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Citation Number: 20

Abstract

Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0" C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the N-(mesyloxy) 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 6 with triethylamine in aqueous acetonitrile.