Regioselective synthesis of isoquino[1,2-b][3]benzazepines (homoprotoberberines) through 11-membered-ring stilbene lactams obtained by radical macrocyclization

Citation
G. Rodriguez et al., Regioselective synthesis of isoquino[1,2-b][3]benzazepines (homoprotoberberines) through 11-membered-ring stilbene lactams obtained by radical macrocyclization, J ORG CHEM, 64(13), 1999, pp. 4830-4833
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
13
Year of publication
1999
Pages
4830 - 4833
Database
ISI
SICI code
0022-3263(19990625)64:13<4830:RSOI(>2.0.ZU;2-B
Abstract
Silylated 11-membered-ring stilbene lactams 3 (E and Z) were easily prepare d by intramolecular addition of an aryl radical to a trimethylsilylacetylen e. Oxidation of their hindered stilbene double bonds with dioxiranes gave o xidative cleavage of their electron-rich aromatic rings. However, reduction of the amide to an amine functionality in both lactams (E and Z) triggers a regioselective [7,6]-transannular cyclization to isoquino[l,2-b][3]benzaz epines (homoprotoberberines).