Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

Katalin Prokai-Tatrai, John A. Zoltewicz, William R. Kem

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.

Original languageEnglish
Pages (from-to)9909-9918
Number of pages10
JournalTetrahedron
Volume50
Issue number33
DOIs
StatePublished - 1994

Keywords

  • Bridged anabasine
  • Conformational analysis
  • Molecular mechanics.
  • Nuclear Overhauser enhancement

Fingerprint Dive into the research topics of 'Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.'. Together they form a unique fingerprint.

  • Cite this