ChemInform Abstract: Heterocyclic Spirocyclohexadienones. Part 1.

Abstract

Heterocyclic Spirocyclohexadienones. Part 1.-The dinaphthylmethane derivative (I) (synthesis given) reacts with paraformaldehyde (II) to yield the spiro-fused cyclohexadienone (III) via intramolecular ipsoaminoalkylation. Hydrogenation of (III) leads to the formation of the spiroketone (IV) and the diastereoisomeric spirocyclic alcohols (V). The perchlorate of (III), (VI), reacts with the alcohols (VII) to give the ethers (VIII). No oximation takes place with hydroxylamine hydrochloride: a mixture of the acridine derivatives (IX) and (X) is formed instead. -(MOEHRLE, H.; SCHAKE, D.; BLUHME-HENSEN, K.; Arch.