The various reactions of heterobicyclic systems, synthesis of isoindoline

Nowadays, most of the chemical researches are focused on the synthesizing of the new compounds possibly having biological activities, besides determining and measuring of these activities. It has been shown that imides and its derivatives like isoindolines which are active precursors of the important compounds in the pharmacological and medicinal researches have antidepressant, anticancer, antimalarial, antibacterial and fungicidal properties (Brana vd., 2001; Zentz vd., 2002). Furthermore, the arylation and alkenization of alkenes in presence of palladium catalyst in organic synthesis named as Heck reaction, keep their currency as very effective catalyzing method in forming carbon-carbon bonds. Recently, the asymmetric Heck-type hydroarylation of specific bicyclic ring systems of alkenes have been examined intensively, because of the easily obtained stereoselective results (Namyslo and Kaufmann, 1997, 1999). This study planned after a wide literature surveys, is consist of four steps. The first step is the synthesizing of tricyclic imides as the starting materials N-(4-methoxyphenyl)-7- oxobicyclo[2.2.1]hept-5-ene-exo-2,3-dicarboximide and N-(4-chlorophenyl)-7-oxobicyclo [2.2.1]hept-5-ene-exo-2,3-dicarboximide, the second one is including Heck-type hydroarylation and domino-Heck reactions of alkenic imides with aryl (hetaryl) halides. The third step is after reducing of these compounds with LiAlH4 and NaBH4 to obtain the new isoindoline derivatives. In the last step, the structure determination of all new compounds by IR, 1H NMR, 13C NMR, DEPT, HETCOR, COSY and MS spectroscopic data, respectively. Keywords: Tricyclic imides, Heck and domino-Heck type hydroarylation reactions, reduction of hydrite, isoindoline derivatives.