Please use this identifier to cite or link to this item:
10.2478/s11532-010-0132-x
Title: | Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative |
Authors: | Pajuste, Karlis Plotniece, Aiva Kore, Kintija Intenberga, Liva Cekavicus, Brigita Kaldre, Dainis Duburs, Gunars Sobolev, Arkadij |
Keywords: | 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 |
Issue Date: | 2011 |
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 |
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. |
DOI: | 10.2478/s11532-010-0132-x |
ISSN: | 1895-1066 |
Appears in Collections: | Research outputs from Pure / Zinātniskās darbības rezultāti no ZDIS Pure |
Files in This Item:
File | Size | Format | |
---|---|---|---|
Use_of_pyridinium_ionic_liquids.pdf | 385.57 kB | Adobe PDF | View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.