Skip to main content
SpringerLink
Log in

Stereochemistry and products of addition of tert-butylisonitrile at the carbonyl group of 3-hydroxypiperidin-4-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The stereochemistry and products of addition of tert-butylisonitrile at the carbonyl group of 3-hydroxypiperidin-4-ones have been studied. A preparative method for synthesis of 3-hydroxyisonipecotic acid derivatives has been developed. The orientation of the carbon containing substituent on the quaternary carbon atom was shown using13C NMR vicinal3JC,H spin couplings.

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. I. Ugi (ed.), Isonitrile Chemistry, Academic Press, New York (1971), p. 133.

    Google Scholar 

  2. W. C. Lumma, J. Org. Chem.,46, 3668 (1981).

    CAS  Google Scholar 

  3. D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber.,121, 507 (1988).

    CAS  Google Scholar 

  4. R. Bossio, St. Marcaccini, R. Pepino, and T. Torroba, Synthesis, No. 8, 783 (1993).

    Google Scholar 

  5. P. Jacobsen, I. M. Labouta, K. Shaumburg, E. Falch, and P. Krogsgaard-Larsen, J. Med. Chem.,10, 1157 (1982).

    Google Scholar 

  6. V. F. Bystrov, Usp. Khim.,41, 512 (1972).

    CAS  Google Scholar 

  7. F. F. Lakhvich, N. B. Khripach, and L. S. Stanishevskeii, Khim. Geterotsikl. Soedin., No. 5, 673 (1993).

    Google Scholar 

  8. S. W. Werhly, A. D. Morchand, and S. Werhly, Interpretation of Carbon-13 NMR Spectra, J. Wiley, Chichester (1988), pp. 79, 126.

    Google Scholar 

Download references

Authors
  1. T. T. Lakhvich
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. F. Lakhvich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. S. Stanishevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Belorussian State University, Minsk 220080. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 523–527, April, 1997.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lakhvich, T.T., Lakhvich, O.F. & Stanishevskii, L.S. Stereochemistry and products of addition of tert-butylisonitrile at the carbonyl group of 3-hydroxypiperidin-4-ones. Chem Heterocycl Compd 33, 448–451 (1997). https://doi.org/10.1007/BF02321391

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02321391

Keywords

Search

Navigation