Synthesis of diverse benzo[1,4]oxazin-3-one-based compounds using 1,5-difluoro-2,4-dinitrobenzene

J Comb Chem. 2007 Jan-Feb;9(1):158-70. doi: 10.1021/cc060094u.

Abstract

This paper discusses the synthesis of benzo[1,4]oxazin-3-one-based compounds from 1,5-difluoro-2,4-dinitrobenzene (1), including benzo[1,4]oxazin-3-ones (5-11) and five novel benzo[1,4]oxazin-3-one-based tricycles: 6-hydroxy-4H-1-oxa-4,5,8-triazaanthracen-3-one (14), 3,8-dihydro-5-oxa-1,3,8-triazacyclopenta-[b]-naphthalene-7-one (15, 17, 21), 3,8-dihydro-5-oxa-1,2,3,8-tetraazacylopenta[b]-naphthalene-7-one (16, 20), 3,8-dihydro-1H-5-oxa-1,3,8-triazacyclopenta[b]-naphthalene-2,7-dione (18, 22), and 5,8-dihydro-4H-1-oxa-4,5,8-triazaanthracene-3,6,7-trione (19). Finally, a chemical library based on 15 was synthesized in parallel solution-phase reactions.

MeSH terms

  • Benzoxazines / chemical synthesis*
  • Chromatography, Liquid
  • Combinatorial Chemistry Techniques / methods*
  • Dinitrofluorobenzene / analogs & derivatives*
  • Dinitrofluorobenzene / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure

Substances

  • Benzoxazines
  • Dinitrofluorobenzene
  • 1,5-difluoro-2,4-dinitrobenzene