STEREOCHEMICAL STUDIES .167. PREPARATION AND STERIC STRUCTURE OF TRICYCLIC AND TETRACYCLIC SATURATED OR PARTIALLY SATURATED 1,3-HETEROCYCLES CONTAINING A SATURATED ISOINDOLONE MOIETY

From cis-2-(p-methylbenzoyl)-1-cyclohexanecarboxylic acid (1) and p-me thylbenzoyl)bicyclo[2.2.1]heptane-2-carboxylic acid (2) with alpha,ome ga-alkylenediamines, the perhydroimidazo[2,1-a]isoindolone (3), the co rresponding perhydropyrimido and perhydrodiazepino derivatives (4) and (5) and their methylene-bridged tetracyclic analogues (6-8) were obta ined. Compound (1) and ethanolamine yielded the perhydro-1,3-oxazolo[2 ,3-a]isoindolone derivative (9), while 1 with 3-amino-1-propanol or 2- aminoethanethiol gave the homologous saturated 1,3-oxazino derivative (10) and thiazoloisoindolone derivative (11), respectively. On boiling in xylene, 9 was transformed to the hydroxyethylisoindolone (12). Fro m 1 and o-phenylene-diamine, the trans-isoindolo[2,1-a]benzimidazole d erivative (13) was formed, while 1 and o-aminothiophenol gave the part ly saturated cis-benzthiazole analogue (14).