Synthesis of heterocyclic geminal nitro azides

Katorov, D. V.; Rudakov, Gennady F.; Zhilin, V. F.

doi:10.1007/s11172-009-0323-9

Cited by 10 publications

(7 citation statements)

References 15 publications

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“…ABNHP‐1 is an ideal structure for the synthesis of energetic derivatives and two energetic molecules, TNTON and ADTON, can be achieved through nitrolysis followed by oxidative coupling transformations (Scheme ). (CF 3 CO) 2 O/HNO 3 was proved to be a very effective nitrifying agent to converting 1 to TNTON in 98 % yield . The successful introduction of both nitro and azide groups into 1,3‐oxazinane skeleton made the further research on thermal behaviors and detonation properties of the unique 1,3‐oxazinane energetic materials possible.…”

Section: Resultsmentioning

confidence: 99%

“…(CF 3 CO) 2 O/ HNO 3 was proved to be a very effective nitrifying agent to converting 1 to TNTON in 98 % yield. [6,7] The successful introduction of both nitro and azide groups into 1,3oxazinane skeleton made the further research on thermal behaviors and detonation properties of the unique 1,3oxazinane energetic materials possible. 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57…”

Section: Synthetic Studies Towards Energetic Compounds Based On 13-omentioning

confidence: 99%

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Synthesis, Characterization and Performance of Promising Energetic Materials Based on 1,3‐Oxazinane

Xue¹,

Bi²,

Zhai³

et al. 2019

ChemPlusChem

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1,3‐oxazinane is an ideal framework for advanced energetic materials because of its compact skeleton and the presence of several modifiable sites. However, investigations on characterization and performance of 1,3‐oxazinane energetic compounds are extremely limited. Two heterocyclic 1,3‐oxazinane molecules were synthesized under different Mannich condensation processes and further reacted to form nitro‐ and azide‐substituted energetic compounds 3,5,5‐trinitro‐1,3‐oxazinane (TNTON) and 5‐azido‐3,5‐dinitro‐1,3‐oxazinane (ADTON), in good yields. Interestingly, the two energetic molecules showed distinct physical properties. ADTON shows an impressive glass transition temperature (Tg) as low as −46 °C with high density, which is highly suitable for rate‐accelerating materials. TNTON exhibits good thermal stabilities (melting point of 89 °C and a decomposition point of 231 °C) and highly insensitive behavior (38 J, 360 N). The theoretical detonation pressure of TNTON is ca. 63 % higher than that of TNT, indicating broad application prospects in melt‐cast explosives.

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Section: Resultsmentioning

confidence: 99%

Section: Synthetic Studies Towards Energetic Compounds Based On 13-omentioning

confidence: 99%

Synthesis, Characterization and Performance of Promising Energetic Materials Based on 1,3‐Oxazinane

Xue¹,

Bi²,

Zhai³

et al. 2019

ChemPlusChem

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“…1,3-Dinitrohexahydropyrimidine was firstly synthesized by Bell and Dunstan in 1966 9 and opened up a new field of cyclic 1,3-dinitramine. Some earlier work has concentrated on the synthesis of nitrohexahydropyrimidine energetic compounds, such as 1,3,5-trinitrohexahydropyrimidine 10 , 1,3,5,5-tetranitrohexahydropyrimidine 11 , 5-azido-1,3,5-trinitrohexahydropyrimidine 12 and 5,5-difluoramine-1,3-dinitrohexa hydropyrimidine 13 . Although these studies have provided profound insights into the syntheses and thermal decomposition mechanism of hexahydropyrimidine derivatives, there is still lacking comprehensive investigations on explosive performance and systematic molecular design for hexahydropyrimidine compounds.…”

Section: Introductionmentioning

confidence: 99%

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Duan

Liu²,

Lu³

et al. 2020

Sci Rep

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In this paper, twelve 1,3-dinitrohexahydropyrimidine-based energetic compounds were designed by introducing various explosopheres into hexahydropyrimidine skeleton. Their geometric and electronic structures, heats of formation (HOFs), energetic performance, thermal stability and impact sensitivity were discussed. It is found that the incorporation of electron-withdrawing groups (–NO2, –NHNO2, –N3, –CH(NO2)2, –CF(NO2)2, –C(NO2)3) improves HOFs of the derivatives and all the substituents contribute to enhancing the densities and detonation properties (D, P) of the title compounds. Therein, the substitution of –C(NO2)3 features the best energetic performance with detonation velocity of 9.40 km s−1 and detonation pressure of 40.20 GPa. An analysis of the bond dissociation energies suggests that N–NO2 bond may be the initial site in the thermal decompositions for most of the derivatives. Besides, –ONO2 and –NF2 derivatives stand out with lower impact sensitivity. Characters with striking detonation properties (D = 8.62 km s−1, P = 35.08 GPa; D = 8.81 km s−1, P = 34.88 GPa), good thermal stability, and acceptable impact sensitivity (characteristic height H50 over 34 cm) lead novel compounds 5,5-difluoramine-1,3-dinitrohexahydropyrimidine (K) and 5-fluoro-1,3,5-trinitrohexahydropyrimidine (L) to be very promising energetic materials. This work provides the theoretical molecular design and a reasonable synthetic route of L for further experimental synthesis and testing.

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“…The interest to non-symmetric 1,3-heterocyclic analogs of cyclohexane, especially to tetrahydro-1,3-oxazines is due to their peculiar structural features [1][2][3][4][5][6][7][8] and valuable pharmacological properties [9][10][11] as well as to their wide application in fine organic synthesis [6,[12][13][14][15][16][17][18][19] and developing of new polymeric materials [20,21]. Dipole moment measurements, NMR studies [1,22,23], and X-ray diffraction analysis [14] have led to conclusion that these compounds predominantly exist in the chair conformation with equatorial (C е ) or axial (C а ) orientation of the N-alkyl group.…”

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confidence: 99%

Conformational analysis of 3-methyltetrahydro-1,3-oxazine

2014

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Conformational analysis of 3-methyltetrahydro-1,3-oxazine has been performed using HF/6-31G(d), PBE/3z, and RI-МР2/λ2 simulation approximations. The potential energy surface contains eight minima. Interconversion of the axial and equatorial chair conformers (main minima) occurs via several independent pathways involving six twist forms. The preferred path presumes direct chair-chair transition via pyramidal inversion of the nitrogen atom.

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Synthesis of heterocyclic geminal nitro azides

Cited by 10 publications

References 15 publications

Synthesis, Characterization and Performance of Promising Energetic Materials Based on 1,3‐Oxazinane

Synthesis, Characterization and Performance of Promising Energetic Materials Based on 1,3‐Oxazinane

Screening for energetic compounds based on 1,3-dinitrohexahydropyrimidine skeleton and 5-various explosopheres: molecular design and computational study

Conformational analysis of 3-methyltetrahydro-1,3-oxazine

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