PREPARATION AND NMR DETERMINATION OF STRUCTURES OF TRICYCLIC, TETRACYCLIC AND PENTACYCLIC ISOINDOLONE DERIVATIVES

From the reactions of 3-endo-benzoyl-6-exo-phenylbicyclo [2.2.1] hepta ne-2-endo-carboxylic acid (2) and alpha,omega-diamines or o-aminopheno l/thiophenol, different tri-, tetra- and pentacyclic phenyl-substitute d norbornane-condensed heterocycles were prepared. With ethylenediamin e, 2 furnished two isomeric imidazolo[2,1-a]isoindolones. In the forma tion of one of them, an endo --> exo isomerizaton was observed. The st ereostructures (configurations and conformations) of the compounds wer e elucidated by H-1 and C-13 NMR spectroscopy, with the aid of routine spectra and also DR, DNOE, DEFT, COLOC and 2D-HSC measurements.