PREPARATION AND STERIC STRUCTURE OF CONDENSED-SKELETON SATURATED DIPHENYL-SUBSTITUTED ISOINDOLONES

The Friedel-Crafts reaction of benzene with cis-4-cyclohexene-1,2-dica rboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexane- carboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine. From 2 with ethylenediamine, the saturated imidazo[2,3- a]isoindolone (5) was prepared, while the reaction of 2 with 1,3-diami nopropane furnished a mixture of two isomeric pyrimido[2,3-a]isoindolo nes (6a,b) differing in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-amino propanol, the oxazino[2,3-a]isoindolone (7) was obtained. The reaction of 2 with cis-2-hydroxymethylcyclohexylamine gave the tetracyclic (8) , while 2 and o-3-hydroxymethylbicyclo[2.2.1]hept-5-enyl-2-amine yield ed the isomers (9a,b), which differ in the mutual positions of the phe nyl group on the quaternary carbon and cyclohexane annelation hydrogen s. H-1- and C-13-nmr spectra and DNOE and 2D-HSC measurements proved t hat the 5-phenyl group is cis-equatorial to the two annelated hydrogen s of the cyclohexane ring.