Synthesis and stereochemical studies of 1- and 2-phenyl-substituted 1,3-oxazino[4,3-a]isoquinoline derivatives

Matthias Heydenreich, Andreas Koch, László Lázár, István Szatmári, Reijo Sillanpää, Erich Kleinpeter, Ferenc Fülöp

Research output: Contribution to journalArticle

15 Citations (Scopus)

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-oxazino[4,3- 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-oxazino[4,3-a]isoquinoline (11), by X-ray diffraction.

Original languageEnglish
Pages (from-to)1951-1959
Number of pages9
JournalTetrahedron
Volume59
Issue number11
DOIs
Publication statusPublished - Mar 10 2003

    Fingerprint

Keywords

  • Isoquinolines
  • Molecular modelling
  • Oxazines
  • Stereochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this