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Synthetic routes towards tetrazolium and triazolium dinitromethylides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Tetrazolium-5-dinitromethylide sodium salt has been prepared (91%) by cyclization of 1-amino-1-hydrazino-2,2-dinitroethene with nitrous acid in water. 5-Imino-1-(hydroxyiminonitromethyl) derivatives were obtained by nitration of 2-(5-amino-1,3-dimethyl-1H-1,2,4-triazol-4-ium-4-yl)- and 2-(5-amino-4-methyl-1H-tetrazolium-1-yl)acetate complex salts. Treatment of 4-methyl-1-(2-oxopropyl)-1-tetrazolium methylsulfate with nitric and sulfuric acid gave methyl (3-nitro-1,2,4-oxadiazol-5-yl)amine (27%) probably via dinitromethylide followed by cyclization and loss of nitrogen.

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REFERENCES

  1. R. W. Millar, R. P. Claridge, J. P. B. Sandall, and C. Thompson, ARKIVOC, issue iii, 19 (2002).

  2. A. Puchala, F. Belaj, J. Bergman, and C. O. Kappe, J. Heterocycl. Chem., 38, 1345 (2001).

    CAS  Google Scholar 

  3. A. J. Bellamy, N. V. Latypov, and P. Goede, J. Chem. Res. (S), 257 (2002).

  4. V. Grakauskas and A. H. Albert, J. Heterocycl. Chem., 18, 1477 (1981).

    CAS  Google Scholar 

  5. A. N. Terpigorev, I. V. Tselinskii, A. V. Makarevich, G. M. Frolova, and A. A. Mel’nikov, J. Org. Chem. (USSR) (Engl. Transl.), 23, 214 (1987).

    Google Scholar 

  6. V. V. Semenov, S. A. Shevelev, and L. G. Mel’nikova, Mendeleev Commun., 58 (1993).

  7. C. G. Newton, W. D. Ollis, and D. E. Wright, J. Chem. Soc., Perkin Trans. 1, 69 (1984).

    Google Scholar 

  8. V. V. Semenov, V. S. Bogdanov, B. S. El’yanov, L. G. Mel’nikova, S. A. Shevelev, V. M. Zhulin, and A. A. Fainzil’berg, Chem. Heterocycl. Compd., 859 (1982).

  9. F. Einberg, J. Org. Chem., 29, 2021 (1964).

    CAS  Google Scholar 

  10. A. R. Katritzky and W. Q. Fan, Heterocycles, 34, 2179 (1992).

    Google Scholar 

  11. A. R. Katritzky, J. Lewis, S. Q. Abbas Rizvi, G. Roch, and E. Lunt, Anal. Quim., 70, 994 (1974); Chem. Abstr., 84, 17100 (1976).

    CAS  Google Scholar 

  12. J. Epsztajn, E. Lunt, and A. R. Katritzky, Tetrahedron, 26, 1665 (1970).

    Article  CAS  Google Scholar 

  13. J. Epsztajn and A. R. Katritzky, Tetrahedron Lett., 4739 (1969).

  14. A. R. Katritzky, D. J. Cundy, and J. Chen, J. Energetic Mat., 11, 345 (1993).

    CAS  Google Scholar 

  15. A. R. Katritzky, D. J. Cundy, and J. Chen, J. Heterocycl. Chem., 31, 271 (1994).

    CAS  Google Scholar 

  16. M. E. Baumann, H. Bosshard, W. Breitenstein, and G. Rist, Helv. Chim. Acta, 69, 396 (1986).

    Article  CAS  Google Scholar 

  17. J.-L. Barascut, P. Viallefont, and J. Daunis, Bull. Soc. Chim. Fr., 1649 (1975).

  18. R. A. Henry and W. G. Finnegan, J. Am. Chem. Soc., 76, 923 (1954).

    Article  CAS  Google Scholar 

  19. T. P. Kofman, G. Y. Kartseva, and M. B. Shcherbinin, J. Org. Chem. (USSR) (Engl. Trans.), 38, 1343 (2002).

    Article  CAS  Google Scholar 

  20. O. P. Shitov, V. L. Korolev, V. S. Bogdanov, and V. A. Tartakovsky, Russ. Chem. Bull. Int. Ed., 695 (2003).

  21. G. M. Sheldrick, Acta Crystallogr., A46, 467 (1990).

    CAS  Google Scholar 

  22. G. M. Sheldrick, SHELXTL, Bruker Analytical X-ray Systems, (1997).

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Authors and Affiliations

  1. Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida, 32611-7200, USA

    A. R. Katritzky, G. L. Sommen, A. V. Gromova & R. M. Witek

  2. Department of Chemistry, University of Canterbury, Christchurch, New Zealand

    P. J. Steel

  3. US Army ARDEC, Picatinny Arsenal, USA

    R. Damavarapu

Authors
  1. A. R. Katritzky
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  2. G. L. Sommen
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  3. A. V. Gromova
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  4. R. M. Witek
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  5. P. J. Steel
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  6. R. Damavarapu
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 127–134, January, 2005.

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Katritzky, A.R., Sommen, G.L., Gromova, A.V. et al. Synthetic routes towards tetrazolium and triazolium dinitromethylides. Chem Heterocycl Compd 41, 111–118 (2005). https://doi.org/10.1007/s10593-005-0116-5

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  • DOI: https://doi.org/10.1007/s10593-005-0116-5

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