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 Citations (Scopus)

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 - 1 Jan 1994

Fingerprint

Anabasine
Quinolizidines
Naphthyridines
Molecular mechanics
Molecular modeling
Ships
Boats
Mechanics
Nuclear magnetic resonance spectroscopy
Conformations
Magnetic Resonance Spectroscopy
Fusion reactions
Nuclear magnetic resonance
Derivatives
piperidine

Keywords

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

Cite this

@article{236050f003094c2c860eecd83605a2e9,
title = "Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.",
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.",
keywords = "Bridged anabasine, Conformational analysis, Molecular mechanics., Nuclear Overhauser enhancement",
author = "Katalin Prokai-Tatrai and Zoltewicz, {John A.} and Kem, {William R.}",
year = "1994",
month = "1",
day = "1",
doi = "10.1016/S0040-4020(01)89606-X",
language = "English",
volume = "50",
pages = "9909--9918",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd",
number = "33",

}

Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study. / Prokai-Tatrai, Katalin; Zoltewicz, John A.; Kem, William R.

In: Tetrahedron, Vol. 50, No. 33, 01.01.1994, p. 9909-9918.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.

AU - Prokai-Tatrai, Katalin

AU - Zoltewicz, John A.

AU - Kem, William R.

PY - 1994/1/1

Y1 - 1994/1/1

N2 - 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.

AB - 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.

KW - Bridged anabasine

KW - Conformational analysis

KW - Molecular mechanics.

KW - Nuclear Overhauser enhancement

UR - http://www.scopus.com/inward/record.url?scp=0028001571&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)89606-X

DO - 10.1016/S0040-4020(01)89606-X

M3 - Article

AN - SCOPUS:0028001571

VL - 50

SP - 9909

EP - 9918

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -