PDF icon Download PDF
Synthesis 2011(17): 2859-2864  
DOI: 10.1055/s-0030-1260148
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Molten-State Nitration of Substituted Imidazoles: New Synthetic Approaches to the Novel Melt-Cast Energetic Material, 1-Methyl-2,4,5-trinitroimidazole

Raja Duddu*a, Mao-Xi Zhanga, Reddy Damavarapu*b, Nathaniel Gelberb
a SAIC, U.S. Army ARDEC, Building 3028, Picatinny Arsenal, NJ 07806, USA
Fax: +1(973)3660092; e-Mail: raja.duddu@us.army.mil;
b U.S. Army ARDEC, Building 3028, Picatinny Arsenal, NJ 07806, USA
Fax: +1(973)7245713; e-Mail: reddy.damavarapu@us.army.mil;
Further Information

Publication History

Received 28 April 2011
Publication Date:
02 August 2011 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

Novel, one-step synthetic routes for the preparation of 1-methyl-2,4,5-trinitroimidazole (MTNI) are described. In addition, a new, molten-state nitration method for the synthesis of 1-methyl-2,4,5-trinitroimidazole is developed.

Key words

imidazoles - 1-methyl-2,4,5-trinitroimidazole - nitration - molten-state - solvent-free

    References

  • 1 Mines RO. Lackey L. Introduction to Environmental Engineering   Prentice Hall; Upper Saddle River NJ: 2009. 
  • 2 Okamoto Y. Chou EJ. Croce M. Freeman D. Roth M. Colitti O. Propellants, Explos., Pyrotech.  1982,  1:  18 
    Search in Google Scholar
  • 3a Damavarapu R, Jayasuriya K, Vladamiroff T, and Iyer S. inventors; US Patent  5387297.  ; Chem. Abstr. 1995, 122, 239709n
  • 3b Duddu R, and Dave PR. inventors; US Patent  6015898. 
  • 3c Duddu R, and Dave PR. inventors; US Patent  6160113. 
  • 3d Dave PR. Duddu R. Yang K. Damavarpu R. Gelber N. Surapaneni R. Gilardi R. Tetrahedron Lett.  2004,  45:  2159 
    Search in Google Scholar
  • 3e Dave PR, Duddu R, Damavarapu R, Gelber R, Yang K, and Surapaneni R. inventors; US Patent 6841690  B1. 
  • 3f Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 6965042  B1. 
  • 3g Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 6998485  B1. 
  • 3h Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 7109359  B1. 
  • 3i Duddu R. Dave PR. Damavarapu R. Surapaneni R. Gilardi R. Synth. Commun.  2005,  35:  2709 
    Search in Google Scholar
  • 3j Damavarapu R, Surapaneni R, Gelber N, Duddu R, Zhang M, and Dave PR. inventors; US Patent  7304164. 
  • 3k Damavarapu R. Surapaneni R. Duddu R. Farohor F. Dave PR. Parrish D. J. Heterocycl. Chem.  2007,  44:  241 
    Search in Google Scholar
  • 3l Duddu R. Dave PR. Damavarapu R. Surapaneni R. Gilardi R. Parrish D. Synth. Commun.  2008,  38:  767 
    Search in Google Scholar
  • 3m Duddu R. Dave PR. Damavarapu R. Surapaneni R. Parrish D. Synth. Commun.  2009,  39:  4282 
    Search in Google Scholar
  • 3n Duddu R. Dave PR. Damavarapu R. Gelber N. Parrish D. Tetrahedron Lett.  2010,  51:  339 
    Search in Google Scholar
  • 4a Breccia A. Cavalleri B. Adams GE. Nitroimidazoles, Chemistry, Pharmacology and Clinical Applications, In NATO Advanced Study Institute Series, Series A 42   Plenum Press; New York: 1982. 
  • 4b Nair MD. Nagarajan K. Prog. Drug Res.  1983,  27:  163 
    Search in Google Scholar
  • 5 Novikov SS. Khmelnitskii LI. Levedev OV. Sevastyanova VV. Epishina LV. Chem. Heterocycl. Compd. (Engl. Transl.)  1970,  6:  465 
    CrossrefSearch in Google Scholar
  • 6a Cho JR. Kim KJ. Cho SG. Kim JK.
    J. Heterocycl. Chem.  2002,  3:  141 
    Search in Google Scholar
  • 6b Wang W. Yang W. Ji Y. Ding F. Huozhayao Xuebao  2008,  31:  32 
    Search in Google Scholar
  • 7 Jadhav HS. Talawar MB. Sivabalan R. Dhavale DD. Asthana SN. Krishnamurthy VN. J. Hazard. Mater.  2007,  143:  192 
    CrossrefSearch in Google Scholar
  • 8a Boyer JH. Nitroazoles. The C-Nitro Derivatives of Five-Membered N- and N,O-Heterocycles, In Organic Nitro Chemistry, Series 1   VCH Publishers; Deerfield Beach / FL: 1986. 
  • 8b Larina L. Lopyrev V. Topics in Applied Chemistry. Nitroazoles: Synthesis, Structure and Applications   Springer; New York: 2009. 
  • 8c Albright LF. Carr RVC. Schmitt RJ. Nitration: Recent Laboratory and Industrial Developments, ACS Symposium Series 623   American Chemical Society; Washington DC: 1996. 
  • 8d Katritzky AR. Scriven EFV. Majumder S. Akhmedova RG. Akhmedov NG. Vakulenko AV. ARKIVOC  2005,  (iii):  179 
    Search in Google Scholar
  • 8e Thottempudi V. Kim TK. Chung KH. Kim JS. Bull. Korean Chem. Soc.  2009,  30:  2152 
    Search in Google Scholar
  • 8f Rajaraman S, and Yaqub U. inventors; US Patent 7608725  B1. 
  • 8g Agrawal JP. Hodgson RD. Organic Chemistry of Explosives   John Wiley & Sons; Chichester: 2007. 
  • 9a Katritzky AR. Cundy DJ. Chen J. J. Energetic Mater.  1993,  11:  345 
    Search in Google Scholar
  • 9b Gao H. Ye C. Gupta OD. Xiao JC. Hiskey MA. Twamley B. Shreeve JM. Chem. Eur. J.  2007,  13:  3853 
    Search in Google Scholar
  • 10a Suwinski J. Salwinska E. Watras J. Widel M. Pol. J. Chem.  1982,  56:  1261 
    Search in Google Scholar
  • 10b Groziak MP. Ding H. Acta Chim. Slov.  2000,  47:  1 
    Search in Google Scholar
  • 11a Yagupol’skii LM. Maletina II. Orda VV. Zh. Org. Khim.  1974,  10:  2226 
    Search in Google Scholar
  • 11b Hakimelahi GH. Sharghi H. Zarrinmayeh H. Khalafi-Nezhad A. Helv. Chim. Acta  1984,  67:  906 
    Search in Google Scholar
  • 11c Effenberger F. Geke J. Synthesis  1975,  40 
  • 12 Dehmlow EV. Richter R. Zhivich AB. J. Chem. Res., Synop.  1993,  504