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

• DOI: 10.2478/s11532-010-0132-x
• Publication Date: 2010-12-15T19:04:08Z
• Authors: Karlis Pajuste; Aiva Plotniece; Kintija Kore; Liva Intenberga; Brigita Cekavicus; Dainis Kaldre; Gunars Duburs; Arkadij Sobolev
• Keywords: Cationic polymerization; Derivative (finance)

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