Dopamine/Serotonin receptor ligands VI. Dibenzg,f-1-oxa-4-Azacycloundecene and Dibenzd,g-12-azacycloundecene: Synthesis of two new heterocyclic ring systems as potential ligand for dopamine receptor subtypes

摘要

2-(2-Hydroxyethyl)-N-2-phenoxyethylbenzamides and 2-(2-hydroxyethyl)-n-2-phenylpropylbenzamides have been prepared from 2-phenoxyethyl-or 2-phenylpropylamines and isochroman-1-one. Applying Bischer-Napieralski reaction, a tetracyclic isoquinolino2,1-d1,4benzoxazepine and a isoquinolino1,2-a2benzazepine could be obtained. The titled compounds representing novel 11 membered heterocycles could be prepared by subsequent ring cleavage under Birch conditions after quaternisation with methyl iodide. They are considered to be ligands for doapmine receptors. NMR spectra data indicate different conformations for the two azacycloundecene deriatives.