Synthesis of a hexahydro-2H-imidazo[4,5-g]isoquinolin-2-one derivative as an isostere of catecholamine-based selective dopamine D-1 antagonists

Add time:09/09/2019    Source:sciencedirect.com

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.

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