A Convenient Mild Two Step Conversion of Imines to Secondary and Tertiary Amides

R Alan Aitken, S V RAUT

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Treatment of DELTA-2-1,2,4-oxadiazolines (4,5-dihydro-1,2,4-oxadiazoles), readily formed by cycloaddition of nitrile oxides to imines, with potassium tert-butoxide leads to cycloreversion of the resulting anions to give a nitrile 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 nitrile oxides similarly affords carboxylic acids and methyl esters.

Original languageEnglish
Pages (from-to)189-190
Number of pages2
JournalSynlett
Issue number3
Publication statusPublished - Mar 1991

Keywords

  • 1.3-DIPOLAR CYCLOADDITIONS
  • NITRILE OXIDES
  • ADDITIONS

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