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Paper | Regular issue | Vol 60, No. 4, 2003, pp.887-898
Published online, 3rd March, 2003
DOI: 10.3987/COM-02-9704
Dopamine/Serotonin Receptor Ligands VI. Dibenz[g,j]-1-oxa-4-azacycloundecene and Dibenz[d,g]-2-azacycloundecene: Synthesis of Two New Heterocyclic Ring Systems as Potential Ligands for Dopamine Receptor Subtypes

Thomas W. Wittig, Christoph Enzensperger, and Jochen Lehmann*

*Institute of Pharmacy, Friedrich-Schiller-University of Jena, Philosophenweg 14, D-07743 Jena, Germany

Abstract

2-(2-Hydroxyethyl)-N-[2-phenoxyethyl]benzamides and 2-(2-hydroxyethyl)-N-[2-phenylpropyl]benzamides have been prepared from 2-phenoxyethyl- or 2-phenylpropylamines and isochroman-1-one. Applying Bischler-Napieralski reaction, a tetracyclic isoquinolino[2,1-d][1,4]benzoxazepine and a isoquinolino[1,2-a][2]benzazepine 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 dopamine receptors. NMR spectral data indicate different conformations for the two azacycloundecene derivatives.