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.
Yuan
Yunyun
Y
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, P. R. China.
Liu
Gang
G
Li
Li
L
Wang
Zhanguo
Z
Wang
Lin
L
D048588:Benzoxazines / Q000138:chemical synthesis*; D002853:Chromatography, Liquid; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004139:Dinitrofluorobenzene / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
D048588:Benzoxazines; D004139:Dinitrofluorobenzene; C002041:1,5-difluoro-2,4-dinitrobenzene