| Affiliation: | (1) Department of General and Inorganic Chemistry, Loránd Eötvös University, H-1518 Budapest, Hungary;(2) Research Group for Structural Chemistry and Spectroscopy, Hungarian Academy of Sciences – Loránd Eötvös University, H-1518 Budapest, Hungary;(3) Institute of Pharmaceutical Chemistry, University of Szeged, H-6701 Szeged, Hungary |
| Abstract: | Summary. t-2-Benzoyl-t-4-phenylcyclohexane-r-1-carboxylic acid reacts with hydrazine to give the saturated 1,7-diphenyl-trans-phthalazin-4(3H)-one. The reaction of the acid with ethylenediamine yields diastereomeric trans-imidazo[2,3-a]isoindoles, which differ in their C-1 configuration. The cyclizations of the acid with cis-2-aminocyclohexane- or 4-cyclohexenemethanol result in trans-isoindolo[2,1-a][3,1]benzoxazines, while in its reactions with the analogous di-endo- and di-exo-norbornane- and -norborneneamino alcohols, the acid gives methylene-bridged isomeric di-endo-norbornanes or a norbornene derivative; the corresponding diastereomeric di-exo derivatives have also been prepared. After isolation, the structures were established by means of 1H and 13C NMR spectroscopy, with application of DIFFNOE, DEPT, HMQC, HMBC, and 2D-COSY techniques. |
