Skip to main content
SpringerLink
Log in

Reactions of 3-azido-1,2,4-triazole with electrophiles

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Alkylation of 3-azido-1,2,4-triazole with oxiranes, bromoacetone, and methyl vinyl ketone furnished a mixture of N-substituted 3- and 5-azido-1,2,4-triazoles, 3-azido compounds prevailing. The same substrate subjected to heterylation with 3,5-dinitro-1,2,4-triazole derivatives reacted selectively at the N1 atom, and its bromination afforded 3-azido-5-bromo-1,2,4-triazole..

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Manchot, W. and Noll, R., Lieb. Ann., 1905, vol. 343, p. 1.

    Google Scholar 

  2. Heitke, B.T. and McCarty, C.G., J. Org. Chem., 1974, vol. 39, p. 1522.

    Google Scholar 

  3. Mel’nikov, V.V., Baeva, L.F., Stolpakova, V.V., Pevzner, M.S., Martynova, M.N., and Gidaspov, B.V., Khim. Geterotsikl. Soed., 1974, p. 1283; Mel’nikov, V.V., Baeva, L.F., Stolpakova, V.V., Pevzner, M.S., and Gidaspov, B.V., Khim. Geterotsikl. Soed., 1977, p. 839.

  4. Pevzner, M.S., Martynova, M.N., and Timofeeva, T.N., Khim. Geterotsikl. Soed., 1974, p. 1288.

  5. Bagal, L.I., Pevzner, M.S., Sheludyakova, N.I., and Kerusov, V.M., Khim. Geterotsikl. Soed., 1970, p. 265.

  6. Octapkovich, A.M., Kofman, T.P., Lisitsyna, L.V., and Pevzner, M.S. Izv. Vuzov, Ser. Khim. i Khim. Tekhnol., 1979, vol. 22, p. 402. Kofman, T.P. and Kartseva, G.Yu., Zh. Org. Khim., 2001, vol. 37, p. 744.

    Google Scholar 

  7. Kofman, T.P., Uspenskaya, T.L., Medvedeva, N.Yu., and Pevzner, M.S., Khim. Geterotsikl. Soed., 1976, p. 991.

  8. Pevzner, M.S., Kofman, T.P., Kibasova, E.N., Sushchenko, L.F., and Uspenskaya, T.L., Khim. Geterotsikl. Soed., 1980, p. 257; Kofman, T.P., and Kartseva, G.Yu., Zh. Org. Khim., 2000, vol. 36, p. 899; Kofman, T.P., Zh. Org. Khim., 2001, vol. 37, p. 1217.

  9. Witkowski, J.T. and Robins, P.K., J. Org. Chem., 1970, vol. 35, p. 2635.

    Google Scholar 

  10. Kofman, T.P., Zykova, G.A., Manuilova, V.I., Pevzner, M.S., and Timofeeva, T.N., Khim. Geterotsikl. Soed., 1974, p. 997; Kofman, T.P., Vasyl’eva, I.V., and Pevzner, M.S., Khim. Geterotsikl. Soed., 1976, p. 1281. Kofman, T.P., Vasyl’eva, I.V., and Pevzner, M.S., Khim. Geterotsikl. Soed., 1977, p. 1407; Kofman, T.P. and Paketina, E.A., Zh. Org. Khim., 1995, 31, p. 1063.

  11. Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, New York: Wiley, 1962.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological Institute, 198013, St. Petersburg, Russia

    T. P. Kofman & K. N. Krasnov

Authors
  1. T. P. Kofman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. N. Krasnov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 11, 2004, pp. 1699–1704.

Original Russian Text Copyright © 2004 by Kofman, Krasnov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kofman, T.P., Krasnov, K.N. Reactions of 3-azido-1,2,4-triazole with electrophiles. Russ J Org Chem 40, 1651–1656 (2004). https://doi.org/10.1007/s11178-005-0074-5

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0074-5

Keywords

Search

Navigation