Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3-oxathiazino[4,3-a]isoquinolines

Ildikó Schuster, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, L. Lázár, F. Fülöp

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side-chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3-oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis1-trans-cis2 type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines.

Original languageEnglish
Pages (from-to)124-137
Number of pages14
JournalJournal of Molecular Structure
Volume888
Issue number1-3
DOIs
Publication statusPublished - Oct 15 2008

Fingerprint

Isoquinolines
Tetrahydroisoquinolines
Oxides
Bearings (structural)
Amino Alcohols
Discrete Fourier transforms
Nuclear magnetic resonance
isoquinoline

Keywords

  • Conformational analysis
  • Fused-ring systems
  • Molecular modelling
  • Phosphorus heterocycles
  • Sulfur heterocycles

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3-oxathiazino[4,3-a]isoquinolines. / Schuster, Ildikó; Koch, Andreas; Heydenreich, Matthias; Kleinpeter, Erich; Lázár, L.; Fülöp, F.

In: Journal of Molecular Structure, Vol. 888, No. 1-3, 15.10.2008, p. 124-137.

Research output: Contribution to journalArticle

Schuster, Ildikó ; Koch, Andreas ; Heydenreich, Matthias ; Kleinpeter, Erich ; Lázár, L. ; Fülöp, F. / Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3-oxathiazino[4,3-a]isoquinolines. In: Journal of Molecular Structure. 2008 ; Vol. 888, No. 1-3. pp. 124-137.
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abstract = "Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side-chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3-oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis1-trans-cis2 type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines.",
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AU - Koch, Andreas

AU - Heydenreich, Matthias

AU - Kleinpeter, Erich

AU - Lázár, L.

AU - Fülöp, F.

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AB - Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side-chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3-oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis1-trans-cis2 type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines.

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