Efficient generation of highly functionalized fused oxazepine frameworks based on a CAN-catalyzed four-component tetrahydropyridine synthesis/ring-closing metathesis sequence

J Org Chem. 2009 Dec 18;74(24):9365-71. doi: 10.1021/jo9021309.

Abstract

1-Allyl(propargyl)-6-allyl(propargyl)oxy-1,4,5,6-tetrahydropyridines, obtained through a CAN-catalyzed four-component reaction, were transformed into highly functionalized pyrido[2,1-b][1,3]oxazepines by ring-closing metathesis (RCM) and ring-closing enyne metathesis (RCEYM) processes, which constitute the first examples of the preparation of 1,3-oxazepine systems using metathesis reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Cerium / chemistry*
  • Cyclization
  • Molecular Mimicry
  • Nitrates / chemistry*
  • Oxazepines / chemical synthesis*
  • Oxazepines / chemistry*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*

Substances

  • Alkynes
  • Nitrates
  • Oxazepines
  • Pyridines
  • cerium(IV) ammonium nitrate
  • Cerium