Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: I. Synthesis of N-nitrobenzimidazol-2-ones

Tatarnikova, E. V.; Sizov, V. V.; Целинский, И. В.

doi:10.1134/s1070428009060128

Cited by 2 publications

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References 2 publications

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“…The components were quantitated by the internal normalization technique using calibration factors. 5,6-Dinitro-2,3-dihydro-1H-benzimidazol-2-one (VI) and 4,5,6-trinitro-2,3-dihydro-1H-benzimidazol-2-one (V) were synthesized according to the procedures described in [1,18]. 1,4,5,6-Tetranitro-2,3-dihydro-1H-benzimidazol-2-one (I).…”

Section: Methodsmentioning

confidence: 99%

“…In the preceding communication [1] we reported on the synthesis of hitherto unknown 1,4,5,6-tetranitro-2,3-dihydro-1H-benzimidazol-2-one (I), 1,3,5,6-tetranitro-2,3-dihydro-1H-benzimidazol-2-one (II), and 1,5,6-trinitro-2,3-dihydro-1H-benzimidazol-2-one (III). In continuation of our studies in this line, in the present work we examined some chemical transformations of N-nitro compounds I-III, namely their rearrangement into the corresponding C-nitro derivatives, which occurred on heating in various organic solvents.…”

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confidence: 96%

“…This rearrangement was used to develop a procedure for the synthesis of 4,5,6,7-tetranitro-1,3-dihydrobenzimidazol-2-one in high yield (90-96%) by nitration of 1,3-dihydrobenzimidazol-2-one, as well as of 5,6-dinitro-and 4,5,6-trinitro-1,3-dihydrobenzimidazol-2-ones, with a small excess of concentrated nitric acid in a mixture with acetic anhydride and acetic acid at 50-60°C.* For communication I, see [1]. …”

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confidence: 99%

“…The thermal rearrangement is an irreversible intramolecular first-order reaction [5,6,[9][10][11]. Its mechanism is likely to involve [1,5]-sigmatropic migration of nitro group, followed by fast tautomerization.…”

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confidence: 99%

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Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

et al. 2009

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N-Nitrobenzimidazol-2-ones readily undergo rearrangement to C-nitro derivatives on heating in various solvents (ethyl acetate, butyl acetate, acetonitrile, acetone, dioxane, o-dichlorobenzene, anisole, acetic acid). This rearrangement was used to develop a procedure for the synthesis of 4,5,6,7-tetranitro-1,3-dihydrobenzimidazol-2-one in high yield (90-96%) by nitration of 1,3-dihydrobenzimidazol-2-one, as well as of 5,6-dinitro-and 4,5,6-trinitro-1,3-dihydrobenzimidazol-2-ones, with a small excess of concentrated nitric acid in a mixture with acetic anhydride and acetic acid at 50-60°C.* For communication I, see [1].

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confidence: 99%

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confidence: 96%

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confidence: 99%

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confidence: 99%

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Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

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N-Trinitroethylamino functionalization of nitroimidazoles: a new strategy for high performance energetic materials

Yin

Zhang

et al. 2013

J. Mater. Chem. A

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An N-functionalized strategy, including N-amination and N-trinitroethylamination, was utilized for the synthesis of nitroimidazole-based energetic materials, giving rise to a new family of highly insensitive Naminonitroimidazoles and oxygen-rich N-trinitroethylaminonitroimidazoles with good to excellent properties. These new energetic materials were fully characterized by IR, 1 H, and 13 C NMR, elemental analysis, and some high performance compounds were further confirmed by 15 N NMR (4a, 4d, 6a, 6b, and 6d), as well as single crystal X-ray diffraction (6a and 6b). N-Functionalization of nitroimidazoles not only gives rise to the N-aminonitroimidazoles as impact insensitive and thermally stable materials (IS > 40 J; T d : 144-308 C), but also provides a series of N-trinitroethylaminoimidazoles, which have favorable densities (1.75-1.84 g cm À3 ), good detonation properties (P: 27.6-35.9 GPa; v D : 7815-8659 m s À1 ), and moderate thermal stabilities (136-172 C). These properties are better than some known energetic compounds, such as TNT (P: 19.5 GPa; v D : 6881 m s À1 ) and TATB (P: 31.2 GPa; v D : 8114 m s À1 ), and are comparable to RDX (P: 35.0 GPa; v D : 8762 m s À1 ). Recently the N-functionalized chemistry of ve-membered azoles has made great progress and many functional groups, such as NO 2 , 14 NH 2 , 15 CH 3 , 16 and CH 2 ONO 2 , 17 have been employed to develop new energetic materials with comprehensively good properties. While NO 2 and CH 2 ONO 2 could improve performance with decreased stabilities, methyl-functionalized compounds are more stable but display poorer performances. Among the N-functionalized methodologies above, N-amination has become one of the most attractive strategies for preparing new energetic materials. The amino products with the additional N-N bond(s) have higher heats of formation, as well as improved detonation properties. Moreover, the amino group can undergo further functionalization, such as nitration, 18 diazotization, 4 or trinitroethylation 15a to provide versatile energetic materials. In general, ve-membered azoles or six-membered azines, with high heats of formation,

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Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: I. Synthesis of N-nitrobenzimidazol-2-ones

Cited by 2 publications

References 2 publications

Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

Nitro derivatives of 1,3-dihydrobenzimidazol-2-one: II. Rearrangement of N-nitrobenzimidazol-2-ones

N-Trinitroethylamino functionalization of nitroimidazoles: a new strategy for high performance energetic materials

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