Synthesis of a Hexahydro-2H-imidazoisoquinolin-2-one Derivative as an Isostere of Catecholamine-based Selective Dopamine D-1 Antagonists

Article abstract of DOI:10.1016/0040-4020(95)98702-J

The synthesis of the racemic hexahydro-2H-imidazo<4,5-g>isoquinolin-2-one 15 (BW2247W94), a 6,7-ureylene isostere of the 6,7-dihydroxy-tetrahydroisoquinoline 1 (BW32C73), has been achieved in ten stages from 4-nitrobenzyl cyanide 5.The key step is a selective reduction of the nitrile 8 to the amine 9, in the presence of nitro and carbamate functional groups.