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

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.Part 8,Allen, A. A., Kurzer, F., Mh. Chem.112, 617 (1978).