Di-isophorone and related compounds. Part 9 1-(substituted)aminodi-isophoranes and their cyclodehydration products

  • Anthony A. Allen
  • Frederick Kurzer
Organische Chemie und Biochemie


The interaction of 1-chlorodi-isophor-2(7)-en-3-one (or its 5,11-bisnorhomologue) with aromatic, heteroaromatic, or saturated heterocyclic amines produces 1-(substituted)aminodi-isophor-2(7)-3n-3-ones by nucleophilic replacement of the bridgehead halogen. Subsequent cyclodehydration affords, in certain examples, substituted 2,3,5,6,7,8-hexahydro-1H,9h-5,8a-methanocycloocta[gh]phenanthridines (“2′,3-dehydro-1-anilinodi-isophor-2,7-dien-3-ols”). Some physical and chemical properties of these novel amines and condensed pentacylic bases are described.


Di-isophorones, 1-arylamino, synthesis and cyclodehydration 2,3,5,6,7,8-Hexahydro-1H,9H-5,8a-methanocycloocta[g,h]phenanthridines Tricyclo[,7]tridecanes 

Di-isophoron und verwandte Verbindungen, 9. Mitt.: 1-Substituierte Aminodi-isophorone und ihre Cyclisierungsprodukte


Die Umsetzung von 1-Chlor-di-isophor-2(7)-en-3-on oder der entsprechenden 5,11-Bis-nor-verbindung mit aromatischen, heteroaromatischen oder gesättigten heterocyclischen Aminen führt durch nucleophile Substitution des Brückenkopf-Halogens zu 1-(substituierten) Aminodi-isophor-2(7)-en-3-onen. Darauffolgende cyclisierende Wasserabspaltung ergibt in gewissen Fällen substituierte 2,3,5,6,7,8-Hexahydro-1H,9H-5,8a-methanocycloocta[gh]phenathridine (“2′,3-Dehydro-1-anilino-di-isophor-2,7-dien-3-ole”). Einige physikalische und chemische Eigenschaften der Amine und dieser neuen Type von kondensierten heterocyclischen Basen werden beschrieben.


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  1. 2.
    Allen, A. A., Duffner, C. R., Kurzer, F. Tetrahedron34, 1247 (1978).Google Scholar
  2. 3.
    International Union of Pure and Applied Chemistry. J. Amer. Chem. Soc.82, 5545 (1960); Nomenclature of Organic Chemistry. 3rd Edition, pp. 31, 35. London: Butterworth. 1971.Google Scholar
  3. 4.
    Chem. Abstracts, Index Guide, Vol. 76–85 (1972–1976); Chemical Abstract Service, Columbus, pp. 1171 et seq (1977).Google Scholar
  4. 5.
    West, W., Matsen, F. A., Becker, R. S., Scott, D. R., Chemical Applications of Spectroscopy (Weissberger, A., West, W., eds.), Part I, 2nd Edition, pp. 63, 267, 358 et seq. New York: Interscience Publishers. 1968; and references given therein.Google Scholar
  5. 6.
    Fieser, L. F., Fieser, M., Reagents for Organic Synthesis, p. 1252. New York: Wiley. 1967.Google Scholar
  6. 7.
    Dannenberg, H., Abhandl. Preuss Akad. Wiss.21, 3 (1939);Woodward, R. B., J. Amer. Chem. Soc.63, 1123 (1941); ibid. J. Amer. Chem. Soc.64, 76 (1942);Fieser, L. F., Fieser, M., Steroids, pp. 15–21. New York: Reinhold. 1959;Dorfman, L., Chem. Rev.53, 47 (1953).Google Scholar
  7. 8.
    Furth, B., Kossanyi, J. Morizur, J. P., Vandewalle, M., Bull. Soc. Chim. Fr.1967, 1428.Google Scholar
  8. 9.
    Allen, A. A., Kurzer, F., Tetrahedron34 1261 (1978).Google Scholar
  9. 10.
    Badische Anilin und Soda Fabrik A.G., German Pat. 947.068; Chem. Abstr.53, 6250 (1959).Google Scholar
  10. 11.
    Warnhoff, E. W., NaNonggai, P., J. Org. Chem.27, 1186 (1962).Google Scholar
  11. 12.
    Bertrand, J. A., Cheung, B., Hammerich, A. D., House, H. O., Reichle, W. T., Vanderveer, D., Zaiko, E. J., J. Org. Chem.42, 1600 (1977).Google Scholar
  12. 13.
    Allen, A. A., Kurzer, F., Langer, S. S., unpublished results.Google Scholar
  13. 14.
    Adams, R., Voorhees, V., Shriner, R. L., Org. Synth. Coll. Vol. I, p. 463. New York: Wiley. 1941.Google Scholar

Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Anthony A. Allen
    • 1
  • Frederick Kurzer
    • 1
  1. 1.Royal Free Hospital School of MedicineUniversity of LondonLondonEngland

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