Synthesis and stereochemistry of 1,3,2-oxazaphosphorino [4,3-A]isoquinolines

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

1,3,2-Oxazaphosphorino[4,3-A]isoquinolines 8a,b, 9a,b and 10a were synthesized by the reactions of homocalycotomine 7 with appropriate dichlorophosphorus derivatives, such as phenylphosphonic dichloride, bis(2-chloroethyl)phosphonic dichloride or phosphoryl chloride. In spite of the blocking effect of the connecting isoquinoline ring system, the oxazaphosphorinane moiety exists as a chair-twist equilibrium, where the conformer ratios are strongly dependent on the P-4 configuration and the stereoelectronic properties of the substituents. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)119-125
Number of pages7
JournalJournal of Molecular Structure
Volume554
Issue number2-3
DOIs
Publication statusPublished - Nov 7 2000

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Isoquinolines
Stereochemistry
dichlorides
stereochemistry
Derivatives
synthesis
seats
chlorides
rings
configurations
phosphoryl chloride
isoquinoline

Keywords

  • Conformational equilibria
  • Crystal structure
  • Oxazaphosphorinane

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

Synthesis and stereochemistry of 1,3,2-oxazaphosphorino [4,3-A]isoquinolines. / Fülöp, F.; Forró, E.; Martinek, T.; Günther, G.; Sillanpää, R.

In: Journal of Molecular Structure, Vol. 554, No. 2-3, 07.11.2000, p. 119-125.

Research output: Contribution to journalArticle

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AU - Fülöp, F.

AU - Forró, E.

AU - Martinek, T.

AU - Günther, G.

AU - Sillanpää, R.

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N2 - 1,3,2-Oxazaphosphorino[4,3-A]isoquinolines 8a,b, 9a,b and 10a were synthesized by the reactions of homocalycotomine 7 with appropriate dichlorophosphorus derivatives, such as phenylphosphonic dichloride, bis(2-chloroethyl)phosphonic dichloride or phosphoryl chloride. In spite of the blocking effect of the connecting isoquinoline ring system, the oxazaphosphorinane moiety exists as a chair-twist equilibrium, where the conformer ratios are strongly dependent on the P-4 configuration and the stereoelectronic properties of the substituents. (C) 2000 Elsevier Science B.V.

AB - 1,3,2-Oxazaphosphorino[4,3-A]isoquinolines 8a,b, 9a,b and 10a were synthesized by the reactions of homocalycotomine 7 with appropriate dichlorophosphorus derivatives, such as phenylphosphonic dichloride, bis(2-chloroethyl)phosphonic dichloride or phosphoryl chloride. In spite of the blocking effect of the connecting isoquinoline ring system, the oxazaphosphorinane moiety exists as a chair-twist equilibrium, where the conformer ratios are strongly dependent on the P-4 configuration and the stereoelectronic properties of the substituents. (C) 2000 Elsevier Science B.V.

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