Skip to main content
Log in

Regioselective synthesis of 9-azabicyclo[4.2.1]- and 9-azabicyclo[3.3.1]nonane derivatives via transannular electrophilic cyclization of N-protected aminocyclooct-4-ene

  • Rapid Communication
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

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

Access this article

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

Instant access to the full article PDF.

References Cited

  • Barluenga, J., Perez-prieto, J., Bayon, A. M. and Asensio, G., The question of the reversibility in the aminomercuration of olefins: Synthesis of N-aryl-9-azabicyclo[4.2.1] and [3.3.1] nonanes by aminomercuration of cis-cis-1,5-cyclooctadiene.Tetrahedron, 40, 1199–1204 (1984).

    Article  CAS  Google Scholar 

  • Barluenga, J., Jimenez, C., Najera, C. and Yus, M., Sulphonamidomercurization of olefins and subsequent reductive demercuration or bromodemercuration.J. Chem. Soc. Perkin Trans. I., 721–725 (1984).

  • Barrelle, M. and Apparu, M., Aminomercuration intramoleculaire d'aziridines cycloocteniques et de leurs aminoalcools precurseurs.Tetrahedron, 33, 1309–1319 (1977).

    Article  CAS  Google Scholar 

  • Bastatle, J. W., Hobson, J. D. and Riddell, W. D., Transannular cyclization of cycloolefinic N-chloroamine. Synthesis of azabicyclic compds.J. Chem. Soc. Perkin Trans. I., 2205–2213 (1972).

  • Bryant, W. M., House, H. O., Pitt, C. G. and Tefertiller, B. A., The mass spectra of derivatives of 3-azabicyclo[3.2.1]octane, 3-azabicyclo[3.3.1] nonane, and 8-azabicyclo[4.3.1]decane.J. Org. Chem., 31, 3120–3127 (1966).

    Article  CAS  Google Scholar 

  • Campbell, H. F., Edwards, O. E., Elder, J. W. and Kolt, R. J., Total synthesis of DL-anatoxin-a and DL-isoanatoxin-a.Pol. J. Chem., 53, 27–36 (1979).

    CAS  Google Scholar 

  • Carmichael, W., Biggs, D. F. and Gorham, P. R., Toxicology and pharmacological action of Anabaena flos-aquae toxin.Science (Washington, D. C.), 187, 542–544 (1975).

    Article  CAS  Google Scholar 

  • Davies, S. G., Polywka, M. E. C. and Tomas, S. E., Stereoselective synthesis of cyclic ethers via bromine assisted epoxide ring expansion.Tetrahedron Lett., 26, 1461–1464 (1985).

    Article  CAS  Google Scholar 

  • Devlin, J. P., Edwards, O. E., Gorham, P. R., Hunter, N. R., Pike, R. K. and Stavric, B., Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h.Can J. Chem., 55, 1367) (1977).

    Article  CAS  Google Scholar 

  • Engler, E. M., Andose, J. D. and Scheeyer, P. von R., Critical evaluation of molecular mechanics.J. Am. Chem. Soc., 95, 8005–8025 (1973).

    Article  CAS  Google Scholar 

  • Harding, K. E. and Tiner, T. H., Electrophilic heteroatom cyclizations: inComprehensive Organic Synthesis, Trost, B. M. (Eds.), Pergamon Press, Oxford, 1991, Vol. 4, pp. 363–421 and references cired therein.

    Google Scholar 

  • Harrowven, D. C. and Pattenden, G., Transannular electrophilic cyclizations: inComprehensive Organic Synthesis, Trost, B. M. (Eds.), Pergamon Press, Oxford, 1991, Vol. 3, pp. 379–411 and references cired therein.

    Google Scholar 

  • Haufe, G., Electrophile and solvent dependent synthesis of cyclic ethers from (Z,Z)-cycloocta-1,5-diene.Tetrahedron Lett., 25, 4365–4368 (1984).

    Article  CAS  Google Scholar 

  • Iida, H., Watanabe, Y. and Kibayashi, C., A new synthetic Route to tropane alkaloids based on [4+2]nitroso cycloaddition to 1,3-cycloheptadienes.J. Org. Chem., 50, 1818–1825 (1985).

    Article  CAS  Google Scholar 

  • Kanne, D. B. and Abood, L. G., Synthesis and biological characterization of pyridohomotropanes. SARs. of conformationally restricted nicotinoids.J. Med. Chem., 31, 506–509 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Kilpatrick, G. J., Identification and distribution of 5-HT3 receptors in rat brain using radioligand binding.Nature, 330, 746–748 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Kim, H. J. and Schlecht, F., Substuent-Directed Oxidation: Regiochemistry and stereochemistry of the addition of hypervalent iodine reagents to cycloalkenols.Tetrahedron Lett., 28, 5229–5232 (1987).

    Article  CAS  Google Scholar 

  • Malpass, J. R. and Smith, C., A simple approach to homotropanes and homotrop-7-enes.Tetrahedron Lett., 33, 273–276 (1992).

    Article  CAS  Google Scholar 

  • Mihailovic, M. L. and Cekovic, Z., Intramolecular oxidative cyclization of alcohols with lead tetraacetate.Synthesis, 209–224 (1970).

  • Parsons, P. J., Camp, N. P., Underwood, J. M. and Harvey, D. M., A short and efficient route to (±)-anatoxin-a.J. Chem. Soc., Chem. Commun., 1461–1462 (1995).

  • Simonidesz, V., Gombos-Wisky, A., Lovacs, G., Baitz-Gacs, E. and Radics, L., A novel functionalization of prostaglandin skeleton. Addition of thallium triacetate to PGF methyl ester.J. Am. Chem. Soc., 100, 6756–6757 (1978).

    Article  CAS  Google Scholar 

  • Stetter, H. and Heckel, K., Verbindugen mit adamantanstruktur ringschluss-reaktionen mit N,N-dibrom-p-toluolsulfonamid.Tetrahedroin Lett., 801–804 (1972).

  • Swern, D. and Labows, J. N., Addition of pseudohalogens to 1,5-cyclooctadiene.J. Org. Chem., 37, 3004–3006 (1972).

    Article  Google Scholar 

  • Toshimiszu, A., Aoai, T., Uemura, S. and Okano, M., Oxyselenation of diolefins with phenyl selenocyanate and copper(II) chloride. Synthesis of cyclic ethers.J. Org. Chem., 46, 3021–3026 (1981).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ham, WH., Kim, KS., Jung, YH. et al. Regioselective synthesis of 9-azabicyclo[4.2.1]- and 9-azabicyclo[3.3.1]nonane derivatives via transannular electrophilic cyclization of N-protected aminocyclooct-4-ene. Arch. Pharm. Res. 19, 432–434 (1996). https://doi.org/10.1007/BF02976392

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02976392

Key words

Navigation