SYNTHESIS AND STRUCTURAL STUDY OF NEW SATURATED ISOINDOL-1-ONE DERIVATIVES

Condensation of 2-p-toluoylcyclohexanecarboxylic acid (1a,b) with prim ary amines gave the corresponding hexahydroisoindol-1-ones (2a-g) in g ood yield. The octahydro derivatives (4a-g) were prepared from cis- an d trans-hexahydro-1-(2H)-phthalazinone (3a,b) by reduction with zinc-h ydrochloric acid via ring contraction. Stereoselective synthesis of ci s-N-phenyloctahydroisoindol-1-one (4h) was performed starting from 2b by reduction with magnesium-methanol at room temperature. Configuratio nal assignments of cis and trans isomers were based on H-1- and C-13-n mr spectroscopic studies.