Advertisement

Russian Journal of Organic Chemistry

, Volume 46, Issue 8, pp 1219–1222 | Cite as

Cyclization of substituted 3,4-diaminopyridines into 1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives during the nitration process

  • N. N. Smolyar
  • A. B. Vasilechko
Article

Abstract

The nitration of pyridine-3,4-diamine, its N,N′-diacetyl derivative, and N 4-alkylpyridine-3,4-diamines with excess nitric acid in concentrated sulfuric acid at 60°C was accompanied by cyclization with formation of the corresponding 1-substituted 4-nitro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxides. 4-Chloro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxide derivatives were obtained under analogous conditions from 2-chloropyridine-3,4-diamine, its N,N′-diacetyl derivative, and 2-chloro-N 4-methylpyridine-3,4-diamine. The nitration of these compounds at 80–90°C gave 4-chloro-7-nitro-1H-[1,2,3]triazolo[4,5-c]pyridine 2-oxides.

Keywords

Diamine Nitration Concentrate Sulfuric Acid Ammonium Carbonate Acetylamino 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Yutilov, Yu.M. and Smolyar, N.N., Russ. J. Org. Chem., 2004, vol. 40, p. 1526.CrossRefGoogle Scholar
  2. 2.
    Terent’ev, P.B. and Stankyavichus, A.P., Mass-spektroskopicheskii analiz biologicheski aktivnykh soedinenii (Mass Spectrometric Analysis of Biologically Active Compounds), Vil’nyus: Mosklas, 1987, p. 140.Google Scholar
  3. 3.
    Hertog, H.J. and Overhoff, A.F.J., Recl. Trav. Chim. Pays-Bas, 1950, vol. 69, p. 468.Google Scholar
  4. 4.
    Temple, C., Smith, B., and Montgomery, J., J. Org. Chem., 1972, vol. 37, p. 3601.CrossRefGoogle Scholar
  5. 5.
    Vasilechko, A.B., Trudy konferentsii “Sovremennye tendentsii v organicheskom sinteze i problemy khimicheskogo obrazovaniya” (Proc. Conf. “Current Trends in Organic Synthesis and Chemical Education Problems”), St. Petersburg, 2005, p. 54.Google Scholar
  6. 6.
    Yutilov, Yu.M. and Svertilova, I.A., Khim. Geterotsikl. Soedin., 1973, p. 138; Yutilov, Yu.M. and Svertilova, I.A., Khim. Geterotsikl. Soedin., 1986, p. 97.Google Scholar
  7. 7.
    Yutilov, Yu.M., Adv. Heterocycl. Chem., 2005, vol. 89, p. 169.CrossRefGoogle Scholar
  8. 8.
    Bremer, O., Justus Liebigs Ann. Chem., 1935, vol. 515, p. 274; Weidenhagen, R. and Weeden, U., Chem. Ber., 1938, vol. 71, p. 2347; Kovaleva, L.I. and Yutilov, Yu.M., Reakt. Osobo Chist. Veshch., 1977, vol. 31, no. 1, p. 4; Misuno, Y., Iton, T., and Saito, K., Chem. Pharm. Bull., 1964, vol. 12, p. 866; Stetsenko, A.V. and Miroshnichenko, N.S., Ukr. Khim. Zh., 1973, vol. 39, p. 703.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  1. 1.Litvinenko Institute of Physical Organic and Coal ChemistryNational Academy of Sciences of UkraineDonetskUkraine

Personalised recommendations