Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative
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Date
2011
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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.
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1,4-Dihydropyridine, 1-Butyl-4-methylpyridinium chloride, Catalysis, Hantzsch synthesis, Ionic liquid, 1.4 Chemical sciences, 1.1. Scientific article indexed in Web of Science and/or Scopus database, General Chemistry, Materials Chemistry
Citation
Pajuste, K, Plotniece, A, Kore, K, Intenberga, L, Cekavicus, B, Kaldre, D, Duburs, G & Sobolev, A 2011, 'Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative', Central European Journal of Chemistry, vol. 9, no. 1, pp. 143-148. https://doi.org/10.2478/s11532-010-0132-x