Multicomponent synthesis of dihydrobenzoxazepinones by coupling Ugi and Mitsunobu reactions

Org Biomol Chem. 2006 Nov 21;4(22):4236-40. doi: 10.1039/b613056a.

Abstract

Various dihydrobenzo[f][1,4]oxazepin-5-ones have been convergently prepared in 2-3 steps by coupling Ugi and Mitsunobu reactions. Two alternative methodologies were used: in the first one the Ugi condensation was followed by a Mitsunobu cyclization (2 steps); in the second one an intermolecular Mitsunobu reaction was followed by a deprotection step and then by an intramolecular Ugi reaction. Also a "convertible" isocyanide was used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Structure
  • Oxazepines / chemical synthesis*
  • Oxazepines / chemistry
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Stereoisomerism

Substances

  • Oxazepines
  • Oxazines