Skip to main content
SpringerLink
Log in

Reduction of 4H-imidazole N-oxides with sodium borohydride

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reduction of derivatives of 4H-imidazole N-oxides with sodium borohydride leads, depending on the presence and position of an N-oxide group, to 1-hydroxyimidazoline or imidazolidine derivatives. Under the same conditions 4H-imidazole N,N′-dioxides form 1,3-dihydroxyimidazolidines. The reduction of 1-hydroxy-2,4,5,5-tetramethyl-3-imidazoline 3-oxide leads to N-(3-oximino-2-methyl-2-butyl) ethylhydroxylamine. It was observed by UV spectroscopy that 1-hydroxy-2-imidazolines exist in a tautomeric equilibrium with 2-imidazoline 3-oxides.

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

Literature cited

  1. L. B. Volodarskii, L. A. Fust, and V. S. Kobrin, Geterotsikl. Soedin., No. 9, 1246 (1972).

    Google Scholar 

  2. V. S. Kobrin, L. B. Volodarskii, L. A. Tikhonova, and Yu. G. Putsykin, Khim. Geterotsikl. Soedin., No. 8, 1087 (1973).

    Google Scholar 

  3. R. Bonnett, R. F. C. Brown, V. M. Clark, J. O. Sutherland, and A. Todd, J. Chem. Soc., 2094 (1959).

  4. M. Lamchen and T. W. Mittag, J. Chem. Soc., C, 2360 (1966).

  5. K. Akagane and G. G. Allan, Chem. Ind., 38 (1974).

  6. K. Krishan and H. Singh, Indian J. Chem., 12, 222 (1974).

    Google Scholar 

  7. J. Baldwin and N. Rogers, Chem. Commun., 524 (1965).

  8. S. O. Chua, M. J. Cook, and A. R. Katritzky, J. Chem. Soc., B, 2350 (1971).

  9. K. M. Fry and E. L. May, J. Org. Chem., 26, 2592 (1961).

    Google Scholar 

  10. P. K. Kadaba, B. Stanovnik, and M. Tisler, Tetrahedron Lett., 3715 (1974).

  11. L. B. Volodarskii and N. Yu. Tormysheva, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim., No. 4, 136 (1976).

    Google Scholar 

  12. L. B. Volodarskii, V. S. Kobrin, and Yu. G. Putsykin, Khim. Geterotsikl. Soedin., No. 9, 1241 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Russia

    V. S. Kobrin & L. B. Volodarskii

Authors
  1. V. S. Kobrin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. B. Volodarskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1557–1561, November, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kobrin, V.S., Volodarskii, L.B. Reduction of 4H-imidazole N-oxides with sodium borohydride. Chem Heterocycl Compd 12, 1280–1284 (1976). https://doi.org/10.1007/BF00470234

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00470234

Keywords

Search

Navigation