Skip to main content
SpringerLink
Log in

Synthesis of 1-hydroxy-2-(N-substituted) azatwistanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reductive amination of bicyclo[3.3.1]nonane-2,6-dione with benzylamine or isopropylamine in the presence of sodium borohydride proceeds with the formation of 1-hydroxy-2-(N-substituted)azatwistanes. When 1-hydroxy-2-benzyl-2-azatwistane is refluxed with acetic anhydride, the ring is opened to give 2-acetoxy-6-acetylbenzylaminobicyclo[3.3.1] nonane. The structures of the synthesized compounds were proved by means of the IR and PMR spectra and the results of elementary analysis.

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. R. C. FortJr., Adamantane: The Chemistry of Diamond Molecules, New York-Basel (1976), p. 267.

    Google Scholar 

  2. N. V. Averina, N. S. Zefirov, P. P. Kadzyauskas, and N. K. Sadovaya, Zh. Org. Khim.,11, 77 (1975).

    Google Scholar 

  3. T. Sasaki, S. Eguchi, T. Kiriyama, and O. Hiroaki, Tetrahedron,30, 2707 (1974).

    Google Scholar 

  4. B. M. Lerman, F. Z. Galin, L. I. Umanskaya, and G. A. Tolstikov, Zh. Org. Khim.,14, 2536 (1978).

    Google Scholar 

  5. D. H. Kim, J. Heterocycl. Chem.,13, 179 (1976).

    Google Scholar 

  6. H. Meerwein, J. Prakt. Chem.,104, 161 (1922).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. V. Kapsukas Vilnius State University, 232006, Vilnius

    P. P. Kadzyauskas, Yu. A. Malinauskene, É. P. Butkus & N. S. Zefirov

Authors
  1. P. P. Kadzyauskas
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. A. Malinauskene
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. É. P. Butkus
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. S. Zefirov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 940–942, July, 1980.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kadzyauskas, P.P., Malinauskene, Y.A., Butkus, É.P. et al. Synthesis of 1-hydroxy-2-(N-substituted) azatwistanes. Chem Heterocycl Compd 16, 727–729 (1980). https://doi.org/10.1007/BF00557747

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00557747

Keywords

Search

Navigation