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

  • Research Article
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Central European Journal of Chemistry

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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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

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

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  1. Karlis Pajuste
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  2. Aiva Plotniece
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  3. Kintija Kore
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  4. Liva Intenberga
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  5. Brigita Cekavicus
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  7. Gunars Duburs
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  8. Arkadij Sobolev
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Correspondence to Arkadij Sobolev.

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Pajuste, K., Plotniece, A., Kore, K. et al. Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative. cent.eur.j.chem. 9, 143–148 (2011). https://doi.org/10.2478/s11532-010-0132-x

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  • DOI: https://doi.org/10.2478/s11532-010-0132-x

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