Tetramic acid and imidazolidinone syntheses via unexpected base induced cyclisations of alanine derived Weinreb amides

Colin Gibson, A.R. Kennedy, R.R. Morthala, J.A. Parkinson, C.J. Suckling

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Reactions of N-protected derivatives of Weinreb amides of alanine with strong base unexpectedly gave tetramic acid derivatives or an imidazolidinone. The tetramic acid derivatives were obtained by unusual cyclisation of N-acyl N-methoxy derivatives of alanine Weinreb amide upon treatment with potassium hexamethyldisilazide and benzyl bromide. In contrast, treatment of a bromobenzylidine alanine Weinreb amide with potassium hexamethyldisilazide gave rise to cyclisation to form an imidazolidinone.
Original languageEnglish
Pages (from-to)7619-7625
Number of pages7
JournalTetrahedron
Volume64
Issue number32
DOIs
Publication statusPublished - 4 Aug 2008

Keywords

  • Weinreb amides
  • tetramic acid
  • imidazolidinone

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