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Synlett 1991; 1991(3): 189-190
DOI: 10.1055/s-1991-20674
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A Convenient Mild Two-Step Conversion of Imines to Secondary and Tertiary Amides

R. Alan Aitken* , Swati V. Raut
  • *Department of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, Scotland
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Publikationsdatum:
07. März 2002 (online)

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Treatment of Δ2-1,2,4-oxadiazolines (4,5-dihydro-1,2,4-oxadiazoles), readily formed by cycloaddition of nitrite oxides to imines, with potassium tert-butoxide leads to cycloreversion of the resulting anions to give a nitrite and the amide anion which can be hydrolysed or alkylated to provide a mild nonoxidising method for the synthesis of secondary or tertiary amides. Deprotonation of the 1,4,2-dioxazoles available from aromatic aldehydes and nitrite oxides similarly affords carboxylic acids and methyl esters.

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