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

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.