Base-induced cycloreversion of nitrile oxide cycloadducts: Conversion of imines into secondary and tertiary amides and aromatic aldehydes into acids without a conventional oxidising agent

R Alan Aitken, S V Raut

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A series of substituted Delta(2)-1,2,4-oxadiazolines(4,5-dihydro-1,2,4-oxadiazoles) 12 have been prepared by 1,3-dipolar cycloaddition of nitrile oxides to imines and are found, upon treatment with KOBu(t), to undergo cycloreversion to give nitriles and amide anions. These can be protonated to give secondary amides or treated in situ with alkyl halides to give tertiary amides in moderate to good overall yield, although the reaction is restricted to examples with an aromatic substituent at the 5-position. The 1,4,2-dioxazoles 15, formed by cycloaddition of benzonitrile oxide to aromatic aldehydes, similarly undergo cycloreversion allowing direct conversion either into substituted benzoic acids or their methyl esters.

Original languageEnglish
Pages (from-to)747-751
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
DOIs
Publication statusPublished - 7 Apr 1996

Keywords

  • 1.3-DIPOLAR CYCLOADDITIONS
  • ADDITIONS

Fingerprint

Dive into the research topics of 'Base-induced cycloreversion of nitrile oxide cycloadducts: Conversion of imines into secondary and tertiary amides and aromatic aldehydes into acids without a conventional oxidising agent'. Together they form a unique fingerprint.

Cite this