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

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

Abstract

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.

Keywords

Di-isophorones, 1-arylamino, synthesis and cyclodehydration 2,3,5,6,7,8-Hexahydro-1H,9H-5,8a-methanocycloocta[g,h]phenanthridines Tricyclo[7.3.1.02,7]tridecanes 

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

Zusammenfassung

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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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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