Preparation and steric structure of condensed-skeleton saturated diphenyl-substituted isoindolones

The Friedel-Crafts reaction of benzene with cis-4-cyclohexene- 1,2-dicarboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexane- carboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetraethylene-1,2-oxazin-8-one (4) with hydroxyl- amine. From 2 with ethylenediamine, the saturated imidazo[2,3-a]isoindolone (5) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-a]isoindolones (6a,b) differing in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-a]isoindolone (7) was obtained (...)