Synthesis and stereochemical studies of 1- and 2-phenyl-substituted 1,3-oxazino[4,3-a]isoquinoline derivatives |
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Authors: | Matthias HeydenreichAndreas Koch László LázárIstván Szatmári Reijo SillanpääErich Kleinpeter Ferenc Fülöp |
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Institution: | a Department of Chemistry, University of Potsdam, POB 69 1553, D-14415 Potsdam, Germany b Institute of Pharmaceutical Chemistry, University of Szeged, H-6701, Szeged, POB 121, Hungary c Department of Chemistry, University of Jyväskylä, FIN-40351 Jyväskylä, Finland |
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Abstract: | Starting from the 1′- or 2′-phenyl-substituted 1-(2′-hydroxyethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline diastereomers 3 and 6, 4-unsubstituted and 4-(p-nitrophenyl)- and 4-oxo-substituted 1-phenyl- and 2-phenyl-9,10-dimethoxy-2H,4H-1,6,7,11b-tetrahydro-1,3-oxazino4,3-a]isoquinolines (7-12) were prepared. The relative configurations and the predominant conformations of the products were determined by NMR spectroscopy, by quantum chemical calculations and, for (2R∗,4S∗,11bR∗)-9,10-dimethoxy-4-(p-nitrophenyl)-2-phenyl-2H,4H-1,6,7,11b-tetrahydro-1,3-oxazino4,3-a]isoquinoline (11), by X-ray diffraction. |
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Keywords: | oxazines isoquinolines stereochemistry molecular modelling |
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