SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDRO-5H-AZEPINO[3,4-B]QUINOLIN-5-ONE DERIVATIVES AS POTENTIAL PERIPHERAL BENZODIAZEPINE-RECEPTOR LIGANDS

Authors
CAPPELLI A ANZINI M VOMERO S
Citation
A. Cappelli et al., SYNTHESIS OF 4-SUBSTITUTED 1,2,3,4-TETRAHYDRO-5H-AZEPINO[3,4-B]QUINOLIN-5-ONE DERIVATIVES AS POTENTIAL PERIPHERAL BENZODIAZEPINE-RECEPTOR LIGANDS, Heterocycles, 38(6), 1994, pp. 1265-1272
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
6
Year of publication
1994
Pages
1265 - 1272
Database
ISI
SICI code
0385-5414(1994)38:6<1265:SO41>2.0.ZU;2-0
Abstract
The synthesis of semirigid analogs of PK 11195, the highly specific pe ripheral benzodiazepine-receptor ligand, is reported. Compound (4) und erwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boilin g toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examina ted.