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Novel Synthetic Route and Characterization of [1,2,5]oxadiazolo- [3,4-e][1,2,3,4]tetrazine 4,6-Di-N-oxide (FTDO)
Received date: 2012-05-16
Revised date: 2012-06-05
Online 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%.
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]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1975 -1980 . DOI: 10.6023/cjoc201205019
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