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

Abstract

A novel synthetic route of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-diN 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% HNO 3 , 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 m ℃ olar ratio of compound 4 and P 2 O 5 was 1∶16, and the volume of solvent was 160 mL/g with a yield of 46.37%.

Synthetic Methods towards Energetic Heterocyclic N-Oxides via Several Cyclization Reactions

“…Yet, the price of tetrafluoroborate nitrate was too expensive, and the nitrated product was difficult to purify. Using 3,4-diaminofurazan (46) as the raw material, compound 48 was obtained by Li Xiangzhi et al [39] via oxidation and condensation, followed by the nitration of 100% HNO 3 and cyclization of P 2 O 5 , leading to the high-purity product FDTO (Scheme 7). The effects of N 2 O 5 , NO 2 BF 4 , 100% HNO 3 , etc.…”

“…It was concluded that using 100% HNO 3 as the nitrating agent, a maximum yield of 99.54% and purity of 99.18% could be achieved. In this reference [39], the cyclization mechanism under the action of P 2 O 5 was discussed (Scheme 8). The nitroamino group in compound 49 was isomerized to produce compound 51 containing a N-hydroxyl group.…”

Progress of Artificial Intelligence in Drug Synthesis and Prospect of Its Application in Nitrification of Energetic Materials

“…Compounds with a high explosive performance, low susceptibility and good chemical and thermal stability are ideal high-performance energetic materials sought by researchers [ 1 , 2 , 3 , 4 ]. The development of high-performance energetic materials to replace poorly performing energetic materials (such as propellants) has far-reaching significance and implications [ 5 , 6 , 7 ]. With the development of energetic materials, a variety of novel energetic materials, synthesis theories and methods have emerged in recent years and new energetic material molecules are constantly constructed.…”