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

20 Citations (Scopus)

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.
LanguageEnglish
Pages529-534
Number of pages6
JournalSynlett
Volume2010
Issue number4
DOIs
Publication statusPublished - Mar 2010

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Lactams
Amides
Amines
Derivatives

Keywords

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

Cite this

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The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction. / Macleod, Fraser; Lang, Stuart; Murphy, John A.

In: Synlett, Vol. 2010, No. 4, 03.2010, p. 529-534.

Research output: Contribution to journalArticle

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