Citation: Li Qiu Wang, Qing Shan Li, Xin Pu, Wei Wei Nie, Xiao Fei Lv, Qiu Rong Li. Syntheses of novel series benzo [1,5] oxazepin-4-one-based compounds from 1,5-difluoro-2,4-dinitrobenzene[J]. Chinese Chemical Letters, ;2008, 19(9): 1021-1023. doi: 10.1016/j.cclet.2008.06.002 shu

Syntheses of novel series benzo [1,5] oxazepin-4-one-based compounds from 1,5-difluoro-2,4-dinitrobenzene

Yanshan University, Qinhuangdao 066004, China

Received Date: 21 January 2008

Fund Project: The authors would like to thank Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College for 1H NMR and Mass spectral determinations, and providing some financial support for this project.

A novel benzo[1,5] oxazepin-4-one skeleton compound and its four derivatives were synthesized effectively from 1,5-difluoro-2,4-dinitrobenzene (DFDNB) under mild conditions. In the process, four intermediates were synthesized by substitutions of the two fluorine atoms and reductions of the meta-dinitro groups in DFDNB respectively. The results showed that the key for synthesizing the intermediates was the substitution of one of the two fluorine atoms in DFDNB by 3-hydroxy butyric acid ethyl ester first, then the other fluorine atom by morpholine, and then the reduction of the meta-dinitro groups in the substitute by HCOONH₄ with Pd/C. The products were purified with silica gel column chromatography, and confirmed by HPLC, LC-MS and ¹H NMR. They should contribute to construct the molecular libraries for therapeutic applications.
- Syntheses,
- Benzo [1,5] oxazepin derivatives,
- DFDNB,
- Substitution,
- Reduction
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