SYNTHESIS OF A HEXAHYDRO-2H-IMIDAZO[4,5-G]ISOQUINOLIN-2-ONE DERIVATIVE AS AN ISOSTERE OF CATECHOLAMINE-BASED SELECTIVE DOPAMINE D-1 ANTAGONISTS

Authors
DENYER CV BUNYAN H LOAKES DM TUCKER J GILLAM J
Citation
Cv. Denyer et al., SYNTHESIS OF A HEXAHYDRO-2H-IMIDAZO[4,5-G]ISOQUINOLIN-2-ONE DERIVATIVE AS AN ISOSTERE OF CATECHOLAMINE-BASED SELECTIVE DOPAMINE D-1 ANTAGONISTS, Tetrahedron, 51(17), 1995, pp. 5057-5066
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
17
Year of publication
1995
Pages
5057 - 5066
Database
ISI
SICI code
0040-4020(1995)51:17<5057:SOAHD>2.0.ZU;2-H
Abstract
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-tet rahydroisoquinoline 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 funct ional groups.