Novel Synthetic Route and Characterization of [1,2,5]oxadiazolo- [3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide (FTDO)

doi:10.6023/cjoc201205019

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1975-1980.DOI: 10.6023/cjoc201205019 Previous Articles Next Articles

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呋咱并[3,4-e]-4,6-二氧化-1,2,3,4-四嗪新法合成与表征

李祥志, 王伯周, 李辉, 李亚南, 毕福强, 霍欢, 樊学忠

西安近代化学研究所西安 710065

收稿日期:2012-05-16 修回日期:2012-06-05 发布日期:2012-06-21
通讯作者: 王伯周 E-mail:wbz600@163.com
基金资助:
国防基础科研计划(No. B0920110051)资助项目.

Novel Synthetic Route and Characterization of [1,2,5]oxadiazolo- [3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide (FTDO)

Li Xiangzhi, Wang Bozhou, Li Hui, Li Yanan, Bi Fuqiang, Huo Huan, Fan Xuezhong

Xi'an Modern Chemistry Research Institute, Xi'an 710065

Received:2012-05-16 Revised:2012-06-05 Published:2012-06-21
Supported by:
Project supported by the National Defense Fundamental Scientific Research (No. B09201100051).

A novel synthetic route of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-di-N-oxide (FTDO) was designed and FTDO was synthesized from 3,4-diaminofurazan (DAF) via the reactions of oxidation, condensation, nitration and cyclization with a total yield of 30.89%. FTDO and its intermediates were characterized by NMR, IR, MS and elemental analysis etc. The mechanism of cyclization was proposed and the conditions for the reaction of nitration and cyclization were optimized. It was found that the optimal conditions for the reaction of nitration were followed as: nitration reagent was 100% HNO₃, the reaction temperature was at 25 ℃ for 2 h with a yield of 99.54%. The optimal conditions for the reaction of cyclization were followed as: the reaction temperature was at 55 ℃, the molar ratio of compound 4 and P₂O₅ was 1∶16, and the volume of solvent was 160 mL/g with a yield of 46.37%.

Key words: [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-di-N-oxide, synthesis, characterization

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Li Xiangzhi, Wang Bozhou, Li Hui, Li Yanan, Bi Fuqiang, Huo Huan, Fan Xuezhong. Novel Synthetic Route and Characterization of [1,2,5]oxadiazolo- [3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide (FTDO)[J]. Chin. J. Org. Chem., 2012, 32(10): 1975-1980.

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呋咱并[3,4-e]-4,6-二氧化-1,2,3,4-四嗪新法合成与表征

Novel Synthetic Route and Characterization of [1,2,5]oxadiazolo- [3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide (FTDO)

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