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

• Authors: Karlis Pajuste , Aiva Plotniece , Kintija Kore , Liva Intenberga , Brigita Cekavicus , Dainis Kaldre , Gunars Duburs , Arkadij Sobolev
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

Hantzsch synthesis; 1,4-dihydropyridine; Ionic liquid; Catalysis; 1-butyl-4-methylpyridinium chloride

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 1
• Pages: 143-148

Dates

published

1 - 2 - 2011

online

16 - 12 - 2010

Contributors

author

Karlis Pajuste

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Aiva Plotniece

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Kintija Kore

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Liva Intenberga

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Brigita Cekavicus

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Dainis Kaldre

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Gunars Duburs

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

author

Arkadij Sobolev

• Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

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Identifiers

DOI

10.2478/s11532-010-0132-x