13490-32-9Relevant articles and documents
A furazan-fused pyrazole N-oxide via unusual cyclization
Tang, Yongxing,He, Chunlin,Shreeve, Jean'ne M.
, p. 4314 - 4319 (2017)
6-Nitro-pyrazolo[3,4-c]furazanate 5-oxide, a new fused anion with high energy, was designed and synthesized via an unusual intramolecular cyclization reaction of 3 by using a mixture of 100% nitric acid and trifluoroacetic anhydride followed by KI reduction. The potassium (6) and nitrogen-rich energetic (9-16) salts were prepared, and fully characterized by IR and multinuclear NMR spectroscopy, elemental analysis, and single-crystal X-ray structuring, 6, 9 and 16. Hydroxylammonium salt (10) has excellent detonation performance but high sensitivity, while 13 and 16 have detonation velocities comparable to 1,3,5-trinitro-1,3,5-triazinane (RDX), which suggests they may have potential application as green primary or secondary explosives.
Nitramino-functionalized tetracyclic oxadiazoles as energetic materials with high performance and high stability: crystal structures and energetic properties
Sun, Qi,Lin, Qiuhan,Lu, Ming
, p. 4321 - 4328 (2018)
A series of tetracyclic energetic materials were developed through the introduction of 1,2,4-oxadiazole into nitramino-1,2,5-oxadiazole. All these thirteen new compounds were fully characterized and seven of them were further confirmed by single crystal X-ray diffraction. Salt formation led to planarization of the parent structure, reduction in lengths, increase in bond-dissociation energies of N-NO2 bonds, and formation of hydrogen bonds, which significantly increased decomposition temperatures from 84 °C (the neutral compound) to 187-303 °C (the energetic salts). Thus, the increase in thermal stability falls in the range of 103-219 °C. To the best of our knowledge, 219 °C is the largest reported increase in thermal stability due to salt formation. In addition, electrostatic surface potentials and noncovalent interactions (π-π stacking) were analyzed to understand structure-property relationships of these compounds. Both theoretical calculations and practical explosive experiments indicate that the dihydroxylammonium salt exhibits better detonation performance than the powerful explosive RDX. The tetracyclic backbone provides these compounds with enhanced stability. Short synthesis steps, low cost, good thermostability, excellent detonation performance, and acceptable mechanical sensitivity highlight the practical applications of these energetic compounds.
Synthesis, crystal structure, and thermal properties of Ni(NH3)4(AFT)2
Wei, Shu-Han,Ma, Xiao,Ding, Zi-Mei,Xu, Kang-Zhen,Gao, Hong-Xu,Huang, Jie,Zhao, Feng-Qi
, p. 582 - 589 (2021)
Ni(NH3)4(AFT)2 [NiC6H16N18O2, AFT = 4-amino-3-(5-tetrazolate)furazan] is synthesized and characterized by elemental analysis and Fourier-transform infrared spectroscopy for the first time. X-ray diffraction measurements are used to determine the crystal structure of compound 1. The results demonstrate that compound 1 crystallized in the orthorhombic crystal system. The nickel(II) ion is six-coordinated by N atoms from two AFT-ligands and four NH3 molecules. Its thermal properties are investigated by differential scanning calorimetry and thermogravimetry-derivative thermogravimetry methods, with the results demonstrating that the differential scanning calorimetry curve exhibits two endothermic and one exothermic processes. The endothermic processes are in the range of 130–510 °C with a peak temperature of 188 °C. The temperature from 230 to 400 °C is the exothermic process in which the peak temperature is 314.58 °C. In addition, Kissinger’s and Ozawa-Doyle’s methods are used for calculating the non-isothermal kinetics parameters. Moreover, the apparent activation energy (E), safety, and thermal stability parameters (TSADT, TTIT, Tb) for Ni(NH3)4(AFT)2 are calculated. In addition, the calculated thermodynamic functions (?S≠, ?H≠, and ?G≠) for the exothermic decomposition process of Ni(NH3)4(AFT)2 are 55.07 J mol?1 K?1, 196.18 kJ mol?1, and 164.90 kJ mol?1, respectively.
Design, synthesis, and biological evaluation of 1,2,5-oxadiazole-3-carboximidamide derivatives as novel indoleamine-2,3-dioxygenase 1 inhibitors
Song, Xiaohan,Sun, Pu,Wang, Jiang,Guo, Wei,Wang, Yi,Meng, Ling-hua,Liu, Hong
, (2020)
Indoleamine 2,3-dioxygenase 1 (IDO1) is the enzyme catalyzing the oxidative metabolism of tryptophan, which accounts for cancer immunosuppression in tumor microenvironment. Several compounds targeting IDO1 have been reported and epacadostat shows strong i
Synthesis of furazane conjugated new heterocycles
Beaudegnies, Renaud,Wendeborn, Sebastian
, p. 2417 - 2424 (2003)
An improved route for the synthesis of 3-(4-aminofurazane-3-yl)-1,2,4-oxadiazole heterocycles using micro-wave irradiation is reported. The preparation of novel 4-(thiazol-4-yl)furazan-3-ylamine, 4-(pyrimidin-4-yl)furazan-3-ylamine and, 4-(pyrazolidin-3-yl)furazan-3-ylamine heterocycles are described.
REARRANGEMENTS OF 5-TRIFLUOROMETHYL-1,2,4-OXADIAZOLES BY ACTION OF AMMONIA AND AMINES
Andrianov, V.G.,Eremeev, A.V.,Sheremet, Yu.B.
, p. 707 (1988)
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Incorporating Energetic Moieties into Four Oxadiazole Ring Systems for the Generation of High-Performance Energetic Materials
Wang, Bohan,Xiong, Hualin,Cheng, Guangbin,Yang, Hongwei
, p. 439 - 447 (2018)
The synthesis of three neutral 3,3′-di(1,2,5-oxadiazol-3-yl)-5,5′-bi(1,2,4-oxadiazole) structures in combination with different energetic moieties such as nitramino, trinitroethylamino, and N-nitrated trinitroethylamino is presented. In addition, a novel family of energetic salts based on 4,4′-([5,5′-bi(1,2,4-oxadiazole)]-3,3′-diyl)-bis(1,2,5-oxadiazol-3-nitramide) is synthesized. The new compounds (4, 6–18) are characterized by IR and multinuclear NMR spectroscopy and elemental analysis. The structures of 4?2 C4H8O2, 9, 13, 15, and 16 are further confirmed by single-crystal X-ray diffraction studies. The thermal stabilities of 4 and 6–18 are determined by differential scanning calorimetry. Most of the new compounds have high densities (1.72–1.93 g cm?3) measured using a gas pycnometer (25 °C). Energetic evaluation indicates that they also have good detonation pressures and velocities (P: 26.4–41.9 GPa; D: 8218–9550 m s?1).
C8N12O8: A promising insensitive high-energy-density material
Wang, Qian,Shao, Yanli,Lu, Ming
, p. 6150 - 6154 (2018)
It is desirable to consider crystal engineering in the research of energetic materials. Herein, we report the synthesis, structure, and energetic properties of a promising explosive, 1,2-bis(3-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl)diazene (5). Based on the single-crystal diffraction data, 5 is nearly coplanar and features face-to-face and wavelike crystal stackings, thereby exhibiting an excellent density of 1.92 g cm-3. Meanwhile, the enthalpy of 5 is as high as 962.4 kJ/mol owing to its extensive high-energy N-N, C-N, and N-O bonds. Compound 5 featuring such a characteristic demonstrates high thermal stability (Td = 256 °C), good mechanical sensitivity (IS, 18 J; FS, 220 N), and superior detonation performance (D, 9240 m s-1; P, 37.5 GPa). The combination of advanced performance and desirable security make it a potential replacement for the commonly used explosives RDX and HMX.
Finding furoxan rings
Chinnam, Ajay Kumar,Imler, Gregory H.,Parrish, Damon A.,Shreeve, Jean'ne M.,Yin, Ping,Yu, Qiong
, p. 5859 - 5864 (2020)
A furoxan ring is derived from a dinitromethyl group. A plausible mechanism is proposed based on 1H, 13C and 15N NMR spectral analysis where a dinitromethyl group releases one molecule of nitric acid to form an unstable nitrile oxide and its dipole isomer which cyclize to a furoxan ring [3,4-bis(4-nitro-1,2,5-oxadizaol-3-yl)-1,2,5-oxadiazole-N-oxide (5)]. This new method of constructing a furoxan (1,2,5-oxadiazole 2-oxide) ring offers a potentially efficient way to obtain excellent energetic materials. In order to stabilize the dinitromethyl-containing precursor [3-(dinitromethyl)-4-nitro-1,2,5-oxadiazole (4)], a series of new energetic salts was synthesized and fully characterized. These materials exhibit high densities, excellent detonation properties and acceptable sensitivities. For example, the hydrazinium salt 9 has a high density of 1.92 g cm-3, a detonation velocity of 9437 m s-1 and a detonation pressure of 41.3 GPa, which approach those properties of CL-20 (ρ, 2.03 g cm-3; vD, 9406 m s-1; P, 44.6 GPa) and which are superior to those of HMX (ρ, 1.90 g cm-3; vD, 9320 m s-1; P, 39.2 GPa).
A promising cation of 4-aminofurazan-3-carboxylic acid amidrazone in desensitizing energetic materials
Zhang, Jichuan,Wang, Zhenyuan,Hsieh, Yunhao,Wang, Binshen,Huang, Haifeng,Yang, Jun,Zhang, Jiaheng
, p. 2519 - 2525 (2020)
For the development of energetic materials, insensitive compounds have attracted considerable attention due to their improved safety and lower cost than those of sensitive energetic compounds during production, transportation, and application. In this study, insensitive 4-aminofurazan-3-carboxylic acid amidrazone was used as a cation to obtain four derivatives which were determined by X-ray single crystal diffraction. It is interesting to note that all four derivatives are insensitive to impact and friction, while the velocities of detonation for derivatives are superior to that of insensitive TATB (1,3,5-triamino-2,4,6-trinitrobenzene). Multi-factors analysis shows that the cation of 4-aminofurazan-3-carboxylic acid amidrazone is a promising furazan-based cation in desensitizing energetic compounds.
2, 3-dioxygenase inhibitor containing substituted amidino structure as well as preparation method and application thereof
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Paragraph 0019; 0025-0027, (2020/10/06)
The invention belongs to the field of drug synthesis, and relates to a 1,2,5-oxadiazole compound csubstituted amidino group as shown in a general formula (I) and pharmaceutically acceptable salts thereof, and a preparation method and medical application o
