Anionic [4+3] heteroannulation of 2-azidoacrylates: a modular synthesis of 2-benzazepin-1-ones

Chem Commun (Camb). 2012 Apr 25;48(33):3999-4001. doi: 10.1039/c2cc30279a. Epub 2012 Mar 16.

Abstract

2-Azidoacrylates undergo [4+3] annulation with phthalides under anionic conditions at low temperatures to furnish 5-hydroxy-2-benzazepinones, the formation of which represents a new concept for the construction of azepines as well as a new reactivity of 2-azidoacrylates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Benzazepines / chemical synthesis*
  • Benzazepines / chemistry*
  • Chemistry Techniques, Synthetic / methods*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Acrylates
  • Benzazepines