引用本文:
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
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
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
Syntheses of novel series benzo [1,5] oxazepin-4-one-based compounds from 1,5-difluoro-2,4-dinitrobenzene
摘要:
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.
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关键词:
- Syntheses
- / Benzo [1,5] oxazepin derivatives
- / DFDNB
- / Substitution
- / Reduction
English
Syntheses of novel series benzo [1,5] oxazepin-4-one-based compounds from 1,5-difluoro-2,4-dinitrobenzene
Abstract:
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.
-
Key words:
- Syntheses
- / Benzo [1,5] oxazepin derivatives
- / DFDNB
- / Substitution
- / Reduction
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