Straightforward synthesis of new tetrahydroquinoline derivatives

Citation
R. Di Fabio et al., Straightforward synthesis of new tetrahydroquinoline derivatives, CAN J CHEM, 78(6), 2000, pp. 809-815
Citations number
22
Categorie Soggetti
Chemistry
Journal title
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
ISSN journal
00084042 → ACNP
Volume
78
Issue
6
Year of publication
2000
Pages
809 - 815
Database
ISI
SICI code
0008-4042(200006)78:6<809:SSONTD>2.0.ZU;2-3
Abstract
To identify novel classes of glycine antagonists, compounds potentially use ful as neuroprotective after stroke, novel substituted tetrahydroquinoline derivatives, satisfying the key pharmacophoric requirements for glycine ant agonists, were designed. To explore the SAR of these compounds an efficient synthetic route was set up exploiting the outstanding reactivity of suitab le N-aryl imine derivatives. In particular an allylmetalation reaction or t he addition of bis(trimethyldisilyl)ketene acetals allowed the preparation of versatile intermediates which were smoothly transformed into the desired bicycle tetrahydroquinoline derivatives by a Heck-type cyclization reactio n.