Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative

Karlis Pajuste, Aiva Plotniece, Kintija Kore, Liva Intenberga, Brigita Cekavicus, Dainis Kaldre, Gunars Duburs, Arkadij Sobolev

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

The synthesis of cationic amphiphilic 1,4-dihydropyridine derivative, potential gene delivery agent is achieved via an efficient multi-step sequence. The key step of this approach is a two-component Hantzsch type cyclisation of 3-oxo-2-[1-phenylmethylidene]-butyric acid dodecyl ester and 3-amino-but-2-enoic acid dodecyl ester utilising bis(2-hydroxyethyl)ether as a solvent and 1-butyl-4-methylpyridinium chloride as a catalyst. The 1,4-dihydropyridine derivative with long alkyl ester chains at positions 3 and 5 of the 1,4-DHP ring - 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-phenyl-1,4-dihydropyridine was obtained in substantially higher yield with respect to classical Hantzsch synthesis. Bromination of this compound followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine.

Original languageEnglish
Pages (from-to)143-148
Number of pages6
JournalCentral European Journal of Chemistry
Volume9
Issue number1
DOIs
Publication statusPublished - 2011
Externally publishedYes

Keywords*

  • 1,4-Dihydropyridine
  • 1-Butyl-4-methylpyridinium chloride
  • Catalysis
  • Hantzsch synthesis
  • Ionic liquid

Field of Science*

  • 1.4 Chemical sciences

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

Fingerprint

Dive into the research topics of 'Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative'. Together they form a unique fingerprint.

Cite this