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The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide)

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Języki publikacji
EN
Abstrakty
EN
The synthesis of LLM-105 (2,6-diamino-3,5-dinitropyrazine 1-oxide) via the direct nitration of 2,6-diaminopyrazine 1-oxide is reported. Two synthetic routes to the starting material 2,6-diaminopyrazine 1-oxide have been investigated. The synthesis of 2,6-diamino-3,5-dinitropyrazine by nitration of 2,6-diaminopyrazine and 2,6-diacetamidopyrazine has also been studied. Whilst mono-nitration of 2,6-diaminopyrazine is very selective, further nitration leads to mixtures of 2,6-diamino-3,5-dinitropyrazine, 6-amino-2-keto-3,5-dinitropyrazine and tetraketopiperazine, the latter predominating in many cases. It was shown that tetraketopiperazine is formed by further reaction of the initially formed 2,6-diamino-3,5-dinitropyrazine. Nitration of 2,6-diacetamidopyrazine does furnish 2,6-diamino-3,5-dinitropyrazine, but the yield is poor.
Rocznik
Strony
33--57
Opis fizyczny
Bibliogr. 12 poz.
Twórcy
autor
Bibliografia
  • [1] Pagoria P.P., Mitchell A.R., Schmidt R.D., Simpson R.L., Garcia F., Forbes J., Cutting J., Lee R., Swansiger R., Hoffman D.M., Synthesis, scale-up and experimental testing of LLM-105 (2,6 diamino-3,5-dinitropyrazine 1-oxide, Insensitive Munitions & Energetic Materials Technology Symposium, San Diego, CA, 1998,1-3-1 to 1-3-5.
  • [2] Tartakovskii V.A., Shitov O.P., Yudin I.L., Myasnikov V.A., Method for the preparation of 2,6-diamino-3,5-dinitropyrazine and 6-chloro-3,5-dinitro-2-methoxypyrazine as an intermediate for its synthesis, SU 1703645 Al (1992).
  • [3] Kerth J., Kuglstatter W., Synthesis and characterisation of 2,6-diamino-3,5-dinitropyrazine 1-oxide (NPEX-1), International Annual Conference oflCT, 32nd (Energetic Materials), 2001, 166/1-166/11.
  • [4] Pagoria P., Lee G.S., Mitchell A.R., Schmidt R.D., The synthesis of amino- and nitro-substituted heterocycles as insensitive energetic materials, Insensitive Munitions & Energetic Materials Technology Symposium, Bordeaux, France, Oct. 8-11,2001,2,655-661.
  • [5] Bala K., AWE Aldermaston; personal communication.
  • [6] (a) Ritter H., Licht H.H., Synthesis and reactions of dinitrated amino and diaminopyridines, J. Heterocydic Chem., 1995, 32, 585-590; (b) Hollins R.A., Merwin L.H., Nissan R.A., Wilson W.S., Giliardi R., Aminonitropyridines and their N-oxides, J. Heterocydic Chem., 1996, 33, 895-904.
  • [7] Shaw J.T., Brotherton C.E., Moon R.W., Winland M.D., Anderson M.D., Kyler K.S., The preparation of 2,6-diaminopyrazine, 2,6-diazidopyrazine and some of their derivatives,/. Heterocydic Chem., 1980, 17, 11-16.
  • [8] (a) Deady L.W., Ring nitrogen oxidation of amino substituted nitrogen heterocycles with m-chloroperbenzoic acid, Synthetic Comm., 1977, 7, 509-514; (b) SatoN., Studies onpyrazines. 12[1]. N-Oxidation of aminopyrazines with m-chloroperbenzoic acid, J. Heterocydic Chem., 1985, 22, 1145-1146.
  • [9] Robke G.J., Behrman E.J., Conversion of aminopyridines into N-oxides by Cam's acid anion (peroxymonosulfate),./. Chem.Res.(S), 1993,412-413.
  • [10] Rhie S.Y., Ryu E.K., An improved procedure for the preparation of aromatic heterocyclic N-oxides, Heterocycles, 1995, 41, 323-328.
  • [11] Barot N., Elvidge J.A., Heterocyclic imines and amines. Part XVI. 2,6-Diaminopyrazine and its 1-oxide from iminodiacetonitrile, J. Chem. Soc. Perkin Transactions I, 1973, 606-612.
  • [12] Elina A.S., Musatova I.A., Syrova G.P., Pyrazines and their N-oxides II. 2-Aminopyrazine N-oxide, Chemistry of Heterocydic Compounds (English version), 1971, 4, 533-535.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT1-0035-0048
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