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

Research output: Contribution to journalArticle

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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

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Isoquinolines
Diamines
Cyclization
Nitrogen
Nuclear magnetic resonance
Population
heliamine
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • Conformation
  • Diamines
  • Isoquinolines
  • Phosphorus heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational analysis of 1,3,2-diazaphosphorino[6,1-a] isoquinolines, a new ring system. / Zalán, Zita; Martinek, T.; Lázár, L.; Fülöp, F.

In: Tetrahedron, Vol. 59, No. 46, 10.11.2003, p. 9117-9125.

Research output: Contribution to journalArticle

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AU - Zalán, Zita

AU - Martinek, T.

AU - Lázár, L.

AU - Fülöp, F.

PY - 2003/11/10

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N2 - 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.

AB - 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.

KW - Conformation

KW - Diamines

KW - Isoquinolines

KW - Phosphorus heterocycles

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