Thermal ring expansion of 2-azidoselenochromenes: first synthetic examples of 1,3-benzoselenazepines

Chem Pharm Bull (Tokyo). 2004 Apr;52(4):485-7. doi: 10.1248/cpb.52.485.

Abstract

The thermolysis of 2-azido-2-tert-butyl-2H-selenochromenes (2a, b), which were easily obtained by the reaction of the corresponding 1-benzoselenopyrylium salts (1) with sodium azide, resulted in a ring expansion to give the novel stable 1,3-benzoselenazepines (5a, b) with denitrogenation in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzazepines / chemical synthesis*
  • Benzopyrans / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Organoselenium Compounds / chemical synthesis*
  • Sodium Azide / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Benzazepines
  • Benzopyrans
  • Indicators and Reagents
  • Organoselenium Compounds
  • Sodium Azide