Chemistry of Urea Nitro Derivatives. Part 3. Reactions of N,N′‐Dinitrourea with Bases.

Abstract

Urea derivatives Urea derivatives P 0490Chemistry of Urea Nitro Derivatives. Part 3. Reactions of N,N'-Dinitrourea with Bases. -Salt formation and complexation of title dinitrourea (I) with several monoand divalent metal ions is studied. Additionally, reaction with amines, ammonia, hydrazine and hydroxylamine proceeds with substitution of one nitro group to afford the corresponding N-nitro-N'-alkyl(amino, hydroxy)urea derivatives (III), (IV) or (V), resp., in moderate to good yields. N-Nitrocarbamates like (VII) are formed under mild conditions on dissolution of dinitrourea in alcohols. -(IL'YASOV, S. G.; LOBANOVA, A. A.; POPOV, N. I.; SATAEV, R. R.; Russ.

Preparation of 1,3‐Diazido‐2‐Nitro‐2‐Azapropane from Urea

“…In the first case, bis(hydroxymethyl)nitramine was derived by the technique reported in the literature 6: a reaction mixture prepared by nitration of urea 7, 8 was directly diluted with water followed by hydrolysis of N , N ′‐dinitrourea in the presence of excess formaldehyde (over 4 M ) at 0–60 °C, with the water layer being extracted with ethyl acetate. The oily product yield constituted 56–60 % calculated as 2 M 1,3‐dihydroxy‐2‐nitrazapropane from 1 M dinitrourea.…”

“…(a) 1,3‐Dihydroxy‐2‐nitro‐2‐azapropane was synthesized by the technique reported in the literature 6. Yield 60 %.…”

“…The following possible synthetic routes to 1,3‐dihydroxy‐2‐nitro‐2‐azapropane are presently described in the literature: from nitramide 4, nitrourethane 5, and urea 6 (Scheme , Scheme , and Scheme ).…”

Synthesis and Characterization of a Thermally and Hydrolytically Stable Energetic Material based on N‐Nitrourea

“…Especially, Nnitroureas are very attractive because mono-nitroureas and di-nitroureas proved to have a good explosive performance [15]. In general, explosives with nitrourea groups usually have high densities (> 1.90 g cm À3 ) [16][17][18][19] and the intramolecular hydrogen bonding within the nitrourea framework can dramatically reduce the impact sensitivity. Due to their potential use as HEDM, numerous cyclic N-nitroureas, like the well-known 1,3,4,6-tetranitroglycouril (TNGU) (Scheme 1), which was first reported by Boileau et al [20] in 1984, were synthesized.…”

Design and Synthesis of Hydrolytically Stable N‐Nitrourea Explosives

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[a] 1IntroductionThe designa nd synthesis of novel energetic materials with higher detonation performance and lower vulnerability is am ajor goali nt he developmento fh igh energy density materials (HEDMs) [1][2][3][4][5][6][7].N itrogen-rich heterocyclic compounds based on N-nitrourea as promising HEDMs have attracted considerable interest due tot heir high densities, high detonation velocities, and excellent oxygenb alance [8][9][10][11].T he nitrourea framework with intramolecular hydrogen bonding usually led to the high density and low impact sensitivity of mono-nitrourea and di-nitrourea. Thus, the design and synthesis of novel nitrourea explosives have become particularly attractive.

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