Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles

Thomas Balalas; Catherine Peperidou; Dimitra J. Hadjipavlou-Litina; Konstantinos E. Litinas

doi:10.1055/s-0035-1560704

Synthesis, Table of Contents

Synthesis 2016; 48(02): 281-292
DOI: 10.1055/s-0035-1560704

paper

Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles^[1]

Thomas Balalas

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

,

Catherine Peperidou

^bDepartment of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece Email: klitinas@chem.auth.gr

,

Dimitra J. Hadjipavlou-Litina*

^bDepartment of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece Email: klitinas@chem.auth.gr

,

Konstantinos E. Litinas*

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece

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Abstract

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Abstract

The room temperature, 1,3-dipolar cycloaddition reactions of the nitrile oxide obtained from (6-piperidin-1-yl-9H-purin-9-yl)acetaldehyde oxime upon phenyliodine(III) bis(trifluoroacetate) treatment with excess unsaturated alcohols as solvent resulted in isoxazoline or isoxazole derivatives in almost quantitative yields. Analogous derivatives were prepared from the reactions of unsaturated phosphates. Preliminary biological tests indicated inhibition of lipid peroxidation for some of the examined compounds.

Key words

modified homo-N-nucleosides - isoxazolines - isoxazoles - 1,3-dipolar cycloaddition reactions - phenyliodine(III) bis(trifluoroacetate) - PIFA

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References

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Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles[1]

Phenyliodine(III) Bis(trifluoroacetate) Mediated Synthesis of 6-Piperidinylpurine Homo-N-nucleosides Modified with Isoxazolines or Isoxazoles^[1]