Synthesis of new enantiopure dimethyl-substituted pyridino-18-crown-6 ethers containing a hydroxymethyl, a formyl, ora carboxyl group at position 4 of the pyridine ring for enantiomeric recognition studies

József Kupai, P. Huszthy, Marianna Katz, Tünde Tóth

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications.

Original languageEnglish
Pages (from-to)134-145
Number of pages12
JournalArkivoc
Volume2012
Issue number5
DOIs
Publication statusPublished - Mar 11 2012

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Ethers
Ether
Oxidation
Derivatives
Molecules
Sensors
pyridine
18-crown-6

Keywords

  • Chiral crown ethers
  • Chiral stationary phases
  • Enantiomeric recognition
  • Fenton-type reaction
  • Macrocycles
  • Pyridino-18-crown-6 ligands

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of new enantiopure dimethyl-substituted pyridino-18-crown-6 ethers containing a hydroxymethyl, a formyl, ora carboxyl group at position 4 of the pyridine ring for enantiomeric recognition studies",
abstract = "An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications.",
keywords = "Chiral crown ethers, Chiral stationary phases, Enantiomeric recognition, Fenton-type reaction, Macrocycles, Pyridino-18-crown-6 ligands",
author = "J{\'o}zsef Kupai and P. Huszthy and Marianna Katz and T{\"u}nde T{\'o}th",
year = "2012",
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T1 - Synthesis of new enantiopure dimethyl-substituted pyridino-18-crown-6 ethers containing a hydroxymethyl, a formyl, ora carboxyl group at position 4 of the pyridine ring for enantiomeric recognition studies

AU - Kupai, József

AU - Huszthy, P.

AU - Katz, Marianna

AU - Tóth, Tünde

PY - 2012/3/11

Y1 - 2012/3/11

N2 - An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications.

AB - An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications.

KW - Chiral crown ethers

KW - Chiral stationary phases

KW - Enantiomeric recognition

KW - Fenton-type reaction

KW - Macrocycles

KW - Pyridino-18-crown-6 ligands

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