Di-isophorone and Related Compounds. Part 9. 1-(Substituted)aminodi-isophoranes and Their Cyclodehydration Products

Article abstract of DOI:10.1007/BF00899780

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)-en-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-methanocyclooctaphenanthridines (''2'3-dehydro-1-anilinodi-isophor-2,7-dien-3-ols'').Some physical and chemical properties of these novel amines and condensed pentacyclic bases are described. - Keywords: Di-isophorones, 1-arylamino, synthesis and cyclodehydration; 2,3,5,6,7,8-Hexahydro-1H,9H-5,8a-methanocyclooctaphenanthridines; Tricyclo<7.3.1.0^2,7>tridecanes