Synthesis and conformational analysis of 1,3,2-diazaphosphorino[6,1-a] isoquinolines, a new ring system

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Abstract

Through ring-closure reactions of N- or 1′-substituted 1-(2′-aminoethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines (5a-e) with phenylphosphonyl dichloride, 1- or 3-substituted 4-phenyl-1,3,4,6,7,11b- tetrahydro-2H-1,3,2-diazaphosphorino[6,1-a]isoquinolin-4-one diastereomers (7a-e and 8a-c,e), the first representatives of a new ring system, were prepared. The diastereomeric ratios in the cyclizations and the conformer (A-E) populations of the nitrogen-bridged tricyclic systems (7 and 8) were strongly influenced by the N- and 1′-substituents of the starting diamines. The conformational analysis of compounds 7 and 8 was performed by 1H, 13C and 31P NMR methods.

Original languageEnglish
Pages (from-to)9117-9125
Number of pages9
JournalTetrahedron
Volume59
Issue number46
DOIs
Publication statusPublished - Nov 10 2003

Keywords

  • Conformation
  • Diamines
  • Isoquinolines
  • Phosphorus heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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