Synthesis and nucleophilic reactions of cyano substituted N-methoxyisoquinolinium salts

Article abstract of DOI:10.1002/ardp.19933261004

Starting from isoquinoline, the cyano substituted N-methoxyisoquinolinium 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-aminals or 1-iminium salts are obtained depending on the amine used, and 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 and with OH^- the corresponding hemiaminal. Conversion with CN^- results in dinitrile derivatives and N-oxides.