SYNTHESIS AND NUCLEOPHILIC REACTIONS OF CYANO SUBSTITUTED N-METHOXYISOQUINOLINIUM SALTS

Starting from isoquinoline, the cyano substituted N-methoxyisoquinolin ium salts 1.1 and 1.4 are prepared. Their behaviour in the presence of O-, C- and N-nucleophiles in different aprotic solvents is examined: from the 1-cyano substituted isoquinolinium derivative 1.1, 1- and 3-a minals or 1-iminium salts are obtained depending on the amine used, an d N-methoxyisocarbostyril 4.1.1 in H2O and OH-. The reaction of the 4- cyano-N-methoxyisoquinolinium salt 1.4 with amines yields 1-aminals an d with OH- the corresponding hemiaminal. Conversion with CN- results i n dinitrile derivatives and N-oxides.