Reactions between Grignard reagents and heterocyclic N-oxides: Stereoselective synthesis of substituted pyridines, piperidines, and piperazines

Research output: Contribution to journalReview article

Abstract

In this perspective we discuss the recent developments of stereoselective synthesis of substituted pyridines, piperidines, and piperazines from cheap and commercially readily available starting materials. Pyridine N-oxides and pyrazine N-oxides are reacted with alkyl, aryl, alkynyl and vinyl Grignard reagents to give a diverse set of heterocycles in high yields. Optically active substituted piperazines are obtained by an asymmetric reaction from pyrazine N-oxides using sparteine as chiral ligand. In addition, a stereoselective synthesis of dienal-oximes from the reaction between pyridine N-oxides and Grignard reagents is presented, which results in a useful intermediate for the synthesis of a diverse set of compounds.

Details

Authors
External organisations
  • Umeå University
  • ACADIA Pharmaceuticals AB
  • University of Gothenburg
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
  • Medicinal Chemistry
Original languageEnglish
Pages (from-to)337-346
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number2
Publication statusPublished - 2011 Jan 21
Publication categoryResearch
Peer-reviewedYes
Externally publishedYes