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Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile. Reaction of the nitrile group with diazomethane

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of the silver salt of (2-methyltetrazol-5-yl)dinitromethane with cyanogen bromide led to the formation of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile. The nitrile group of the latter was capable of entering into 1,3-dipolar cycloaddition with diazomethane, giving a mixture of isomeric 2-methyl-5-[(N-methyl-1,2,3-triazol-4-yl)dinitromethyl]tetrazoles that were separated by column chromatography. Upon treatment with an alcohol solution of potassium hydroxide, denitration of the cycloaddition products occurred and was accompanied by salt formation, leading to the potassium salts of 2-methyl-5-[(N-methyl-1,2,3-triazol-4-yl)(aci-nitro)methyl]tetrazoles.

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References

  1. S. G. Zlotin, G N. Varnaeva, and O. A. Luk’yanov, Usp. Khim., 58, 796 (1989). [Russ. Chem. Rev., 58, 470 (1989).]

    Article  CAS  Google Scholar 

  2. G. A. Shvekhgeimer, V. I. Zvolinskii, and K. I. Kobrakov, Khim. Geterotsikl. Soedin., 435 (1986). [Chem. Heterocycl. Сompd., 22, 353 (1986).]

    Google Scholar 

  3. E. V. Ratsino, L. M. Andreeva, K. V. Altukhov, and V. V. Perekalin, Zh. Org. Khim., 10, 728 (1974).

    CAS  Google Scholar 

  4. A. G. Tyrkov, E. Yu. Akimova, and E. V. Neretina, Zh. Org. Khim., 33, 1883 (1997). [Russ. J. Org. Chem., 33, 1800 (1997).]

    Google Scholar 

  5. T. D. Ladyzhnikova, A. G. Tyrkov, N. A. Solov’ev, and K. V. Altukhov, Zh.. Org. Khim., 25, 444 (1989).

    CAS  Google Scholar 

  6. A. G. Tyrkov and B. G. Suikhanova, Zh. Org. Khim., 35, 1330 (1999). [Russ. J. Org. Chem., 35, 1299 (1999).]

    Google Scholar 

  7. T. D. Meshkov and Z. I. Demireva, Zh. Org. Khim., 21, 1884 (1985).

    Google Scholar 

  8. C. O. Parker, US Pat. Appl. 2925434; RZhKHim., 12L66 (1961).

  9. Z. I. Demireva, A. S. Polyanskaya, I. Mladenov, and V. V. Perekalin, Zh. Org. Khim., 12, 1192 (1976).

    CAS  Google Scholar 

  10. J. L. Chaille and R. W. Walker, US. Pat. Appl. 3450583; Chem. Abstr., 71, 51834 (1969).

    Google Scholar 

  11. C. O. Parker, US Pat. Appl. 3415867; RZhKhim., 11, 11N147P (1970).

  12. C. O. Parker, W. D. Emmons, H. A. Rolewicz, and K. S. McCallum, Tetrahedron, 17, 79 (1962).

    Article  CAS  Google Scholar 

  13. V. Thottempudi and J. M. Shreeve, Synthesis, 1253 (2012).

  14. H. Feuer and C. Savides, J. Am. Chem. Soc., 81, 5826 (1959).

    Article  CAS  Google Scholar 

  15. Ch. Grundmann, R. K. Bansal, and P. S. Osmanski, Lieb. Ann. Chem., 898 (1973).

  16. A. Hantzsch and A. Rickenberger, Ber. Dtsch. Chem. Ges., 32, 628 (1899).

    Article  CAS  Google Scholar 

  17. I. A. Shevtsova and A. G. Tyrkov, Zh. Org. Khim., 43, 1740 (2007). [Russ. J. Org. Chem., 43, 1742 (2007).]

    Google Scholar 

  18. M. A. Abdel’rakhim and A. G. Tyrkov, Khim. Geterotsikl. Soedin., 7, 1192 (2012). [Сhem. Heterocycl. Compd., 48, 1111 (2012).]

    Google Scholar 

  19. V. V. Semenov and S. A. Shevelev, Mendeleev Commun., 20, 332 (2010).

    Article  CAS  Google Scholar 

  20. V. V. Semenov, B. I. Ugrak, S. A. Shevelev, M. I. Kanishchev, A. T. Baryshnikov, and A. A. Fainzil’berg, Izv. Akad. Nauk, Ser. Khim., 8, 1827 (1990).

    Google Scholar 

  21. A. V. Shchastin, B. L. Korsunskii, T. I. Godovikova, and V. P. Lodygina, Zh. Prikl. Khim., 82, 1650 (2009). [Russ. J. Appl. Chem., 82, 1802 (2009).]

    Google Scholar 

  22. V. A. Ostrovskii, M. S. Pevzner, T. P. Kofman, M. B. Shcherbinin, and I. V. Tselinskii, in: O. A. Attanasi and D. Spinelli (editors), Targets in Heterocyclic Systems, Vol. 3, (1999), p. 467.

  23. V. A. Ostrovskii, G. I. Koldobskii, and R. E. Trifonov, in: A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, and R. J. K. Taylor (editors), Comprehensive Heterocyclic Chemistry III, Vol. 6, Elsevier, Oxford (2008), p. 257.

  24. V. A. Ostrovskii, R. E. Trifonov, and E. A. Popova, Izv. Akad. Nauk, Ser. Khim., 4, 765 (2012). [Rus. Chem. Bull., Int. Ed., 61, 768 (2012).]

    Google Scholar 

  25. G. I. Koldobskii and V. A. Ostrovskii, Usp. Khim., 63, 847 (1994). [Russ. Chem. Rev., 63, 797 (1994).]

    Article  CAS  Google Scholar 

  26. A. N. Terpigorev, I. V. Tselinskii, A. V. Makarevich, G. M. Frolova, and A. A. Mel’nikov, Zh. Org. Khim., 23, 244 (1987).

    CAS  Google Scholar 

  27. K. V. Altukhov and V. V. Perekalin, Usp. Khim., 45, 2050 (1976). [Russ. Chem. Rev., 45, 1052 (1976).]

    Article  CAS  Google Scholar 

  28. S. A. Shevelev, Usp. Khim., 39, 1773 (1970). [Russ. Chem. Rev., 39, 844 (1970).]

    Article  CAS  Google Scholar 

  29. S. A. Shevelev, I. L. Dalinger, V. M. Vinogradov, and A. F. Fainzil’berg, Izv. Akad. Nauk, Ser. Khim., 1816 (1990).

  30. T. M. Klapotke and F. X. Steemann, Propellants, Explos., Pyrotech., 35, 114 (2010).

  31. K.-Z. Xu, H. Zhang, P. Liu, J. Huang, Y.-H. Ren, B.-Z. Wang, and F.-Q. Zhao, Propellants, Explos., Pyrotech., 37, 653 (2012).

  32. K. Karaghiosoff, T. M. Klapötke, P. Mayer, C. Miró Sabaté, A. Penger, and J. M. Welch, Inorg. Chem., 47, 1007 (2008).

    Article  CAS  Google Scholar 

  33. Z. Zeng, H. Gao, B. Twamley, and J. M. Shreeve, J. Mater. Chem., 17, 3819 (2007).

    Article  CAS  Google Scholar 

  34. C. O. Parker, Tetrahedron, 17, 109 (1962).

    Article  CAS  Google Scholar 

  35. V. I. Slovetskii, V. A. Shlyapochnikov, S. A. Shevelev, A. A. Fainzil’berg, and S. S. Novikov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 2, 330 (1961).

    Google Scholar 

  36. V. A. Shlyapochnikov, in: V. P. Ivshin (editor), Vibrational Spectra of Aliphatic Nitro Compounds [in Russian], Mariiskii Gos. Un-t, Yoshkar-Ola (2007).

  37. T. D. Ladyzhnikova, N. A. Solov’ev, K. V. Altukhov, and V. V. Perekalin, Zh.. Org.. Khim., 24, 644 (1988).

    CAS  Google Scholar 

  38. A. G. Tyrkov, Thesis for Doct. Chem. Sci. [in Russian], Saratov (2005).

  39. J. T. Larkins, F. E. Saalfeld, and L. Kaplan, Org. Mass Spectrom., 2, 213 (1969).

    Article  CAS  Google Scholar 

  40. C. Pedersen, Acta Chem. Scand., 13, 888 (1959).

    Article  CAS  Google Scholar 

  41. M. A. Khan and B. M. Lynch, J. Heterocycl. Chem. 7, 1237 (1970).

    Article  CAS  Google Scholar 

  42. A. V. Maksikova, G. P. Sukhanov, L. I. Vereshchagin, and G. A. Gareev, Izv. Vuzov. Khimiya i Khim. Tekhnologiya, 27, 172 (1984).

    CAS  Google Scholar 

  43. A. G. Tyrkov, N. A. Solov’ev, T. D. Ladyzhnikova, and K. V. Altukhov, Zh. Org. Khim., 40, 1198 (2004). [Russ. J. Org. Chem., 40, 1151 (2004).]

    Google Scholar 

  44. A. L. Fridman, Yu. N. Senichev, F. A. Gabitov, and E. A. Ponomareva, Zh. Obshch. Khim., 38, 1902 (1968).

    CAS  Google Scholar 

  45. A. I. Ivanov, V. I. Slovetskii, S. A. Shevelev, V. I. Erashko, A. A. Fainzil’berg, and S. S. Novikov, Zh. Fiz. Khim., 9, 2298 (1966).

    Google Scholar 

  46. A. N. Kost (editor), Syntheses of Organic Compounds [Russian translation], Vol. II, Izd. Inostr. Lit., Moscow (1949), p. 123.

  47. A. N. Kost (editor), General Practical Guide to Organic Chemistry [Russian translation], Mir, Moscow (1965), p. 532.

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Correspondence to A. G. Tyrkov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 763-771, May, 2013.

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Tyrkov, A.G., Abdelraheem, M.A. Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile. Reaction of the nitrile group with diazomethane. Chem Heterocycl Comp 49, 712–719 (2013). https://doi.org/10.1007/s10593-013-1302-5

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