The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

Fraser Macleod, Stuart Lang, John A. Murphy

Research output: Contribution to journalArticle

21 Citations (Scopus)
128 Downloads (Pure)

Abstract

2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.
Original languageEnglish
Pages (from-to)529-534
Number of pages6
JournalSynlett
Volume2010
Issue number4
DOIs
Publication statusPublished - Mar 2010

Keywords

  • Aubé-Schmidt
  • rearrangement
  • azide
  • heterocycle
  • bridged amide
  • medium-ring amine
  • medium-ring amide

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