Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems

Zita Zalán, T. Martinek, L. Lázár, Reijo Sillanpää, F. Fülöp

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[5, 4-a]isoquinoline-3-oxides (13 and 14), 1,6,11,11a-tetrahydro-4H-1,3,4,2- oxadiazaphosphino[4,5-b]isoquinoline-3-oxides (15 and 16) and 1,6,7,8,9,9a-hexahydro-4H-pyrido[1,2-d][1,3,4,2]oxadiazaphosphinane-3-oxides (17 and 18), the first representatives of these ring systems, were prepared. NMR and X-ray diffraction studies revealed that, independently of the P-substituent and the relative configuration of the phosphorus atom, 13, 14, 17 and 18 could be characterized by trans-connected hetero rings and the chair conformation of the 1,3,4,2-oxadiazaphosphinane moiety, while the stereochemistry of the connection of the hetero rings in the 1,3,4,2-oxadiazaphosphinanes linearly fused to tetrahydroisoquinoline (15 and 16) was found to be dependent on the P-configuration relative to that of the carbon at the annelation.

Original languageEnglish
Pages (from-to)2883-2891
Number of pages9
JournalTetrahedron
Volume62
Issue number12
DOIs
Publication statusPublished - Mar 20 2006

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Tetrahydroisoquinolines
Oxides
Stereochemistry
Cyclization
X-Ray Diffraction
Phosphorus
Conformations
Carbon
Alcohols
Nuclear magnetic resonance
X ray diffraction
Atoms
piperidine
isoquinoline

Keywords

  • Conformation
  • Hydrazino alcohols
  • Isoquinolines
  • Phosphorus heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems. / Zalán, Zita; Martinek, T.; Lázár, L.; Sillanpää, Reijo; Fülöp, F.

In: Tetrahedron, Vol. 62, No. 12, 20.03.2006, p. 2883-2891.

Research output: Contribution to journalArticle

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T1 - Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems

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AU - Sillanpää, Reijo

AU - Fülöp, F.

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N2 - Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[5, 4-a]isoquinoline-3-oxides (13 and 14), 1,6,11,11a-tetrahydro-4H-1,3,4,2- oxadiazaphosphino[4,5-b]isoquinoline-3-oxides (15 and 16) and 1,6,7,8,9,9a-hexahydro-4H-pyrido[1,2-d][1,3,4,2]oxadiazaphosphinane-3-oxides (17 and 18), the first representatives of these ring systems, were prepared. NMR and X-ray diffraction studies revealed that, independently of the P-substituent and the relative configuration of the phosphorus atom, 13, 14, 17 and 18 could be characterized by trans-connected hetero rings and the chair conformation of the 1,3,4,2-oxadiazaphosphinane moiety, while the stereochemistry of the connection of the hetero rings in the 1,3,4,2-oxadiazaphosphinanes linearly fused to tetrahydroisoquinoline (15 and 16) was found to be dependent on the P-configuration relative to that of the carbon at the annelation.

AB - Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[5, 4-a]isoquinoline-3-oxides (13 and 14), 1,6,11,11a-tetrahydro-4H-1,3,4,2- oxadiazaphosphino[4,5-b]isoquinoline-3-oxides (15 and 16) and 1,6,7,8,9,9a-hexahydro-4H-pyrido[1,2-d][1,3,4,2]oxadiazaphosphinane-3-oxides (17 and 18), the first representatives of these ring systems, were prepared. NMR and X-ray diffraction studies revealed that, independently of the P-substituent and the relative configuration of the phosphorus atom, 13, 14, 17 and 18 could be characterized by trans-connected hetero rings and the chair conformation of the 1,3,4,2-oxadiazaphosphinane moiety, while the stereochemistry of the connection of the hetero rings in the 1,3,4,2-oxadiazaphosphinanes linearly fused to tetrahydroisoquinoline (15 and 16) was found to be dependent on the P-configuration relative to that of the carbon at the annelation.

KW - Conformation

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