PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2011 | 9 | 1 | 143-148
Article title

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

Content
Title variants
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. [...]
Publisher

Journal
Year
Volume
9
Issue
1
Pages
143-148
Physical description
Dates
published
1 - 2 - 2011
online
16 - 12 - 2010
Contributors
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
author
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
author
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
author
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia
  • Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia, arkady@osi.lv
References
  • [1] T. Welton, Coord. Chem. Rev. 248, 2459 (2004) http://dx.doi.org/10.1016/j.ccr.2004.04.015[Crossref]
  • [2] M.J. Earle, K.R. Seddon, Pure Appl. Chem. 72, 1391 (2000) http://dx.doi.org/10.1351/pac200072071391[Crossref]
  • [3] P. Wasserscheid, W. Keim, Angew. Chem., Int. Ed. Engl. 39, 3772 (2000)
  • [4] J. Ranke, K. Molter, F. Stock, U. Bottin-Weber, J. Poczobutt, J. Hoffmann, B. Ondruschka, J. Filser, B. Jastorff, Ecotoxicol. Environ. Saf. 58, 396 (2004) http://dx.doi.org/10.1016/S0147-6513(03)00105-2[Crossref]
  • [5] A.H. Azizov, R.V. Aliyeva, E.S. Kalbaliyeva, M. Ibrahimova, J. Appl. Catal. A. 375, 70 (2010) http://dx.doi.org/10.1016/j.apcata.2009.12.019[Crossref]
  • [6] D.J. Triggle, Biochem. Pharmacol. 78, 217 (2009) http://dx.doi.org/10.1016/j.bcp.2009.02.015[Crossref]
  • [7] A. Zicmanis, A. Hinica, S. Pavlovica, M. Klavins, Latv. Kim. Z. 3, 235 (2009)
  • [8] S.J. Ji, Z.Q. Jiang, J. Lu, T.P. Loh, Synlett 5, 831 (2004) http://dx.doi.org/10.1055/s-2004-820035[Crossref]
  • [9] L. Ming, G.W. Si, W.L. Rong, L.Y. Feng, Y.H. Zheng, J. Mol. Catal. A: Chem. 258, 133 (2006) http://dx.doi.org/10.1016/j.molcata.2006.05.028[Crossref]
  • [10] N. Tewari, N. Dwivedi, R.P. Tripathi, Tetrahedron Lett. 45, 9011 (2004) http://dx.doi.org/10.1016/j.tetlet.2004.10.057[Crossref]
  • [11] L. Xinzhong, E. Wumanjiang, J. Mol. Catal. A: Chem. 279, 159 (2008) http://dx.doi.org/10.1016/j.molcata.2007.08.032[Crossref]
  • [12] B. Ni, Q. Zhang, A.D. Headley, Tetrahedron Lett. 49, 1249 (2008) http://dx.doi.org/10.1016/j.tetlet.2007.12.024[Crossref]
  • [13] X. Zhao, Y. Gu, J. Li, H. Ding, Y. Shan, Catal. Commun. 9, 2179 (2008) http://dx.doi.org/10.1016/j.catcom.2008.04.020[Crossref]
  • [14] Z. Duan, Y. Gu, J. Zhang, L. Zhu, Y. Deng, J. Mol. Catal. A: Chem. 250, 163 (2006) http://dx.doi.org/10.1016/j.molcata.2006.01.035[Crossref]
  • [15] E. Xanthakis, M. Zarevucka, D. Saman, M. Wimmerova, F.N. Kolisis, Z. Wimmer, Tetrahedron: Asymmetry 17, 2987 (2006) http://dx.doi.org/10.1016/j.tetasy.2006.10.045[Crossref]
  • [16] A. Sobolev, M.C.R. Franssen, B. Vigante, B. Cekavicus, R. Zhalubovskis, H. Kooijman, A.L. Spek, G. Duburs, Ae. de Groot, J. Org. Chem. 67, 401 (2002) http://dx.doi.org/10.1021/jo0104025[Crossref]
  • [17] Z. Hyvönen, A. Plotniece, I. Reine, B. Chekavichus, G. Duburs, A. Urtti, Biochim. Biophys. Acta 1509, 451 (2000) http://dx.doi.org/10.1016/S0005-2736(00)00327-8[Crossref]
  • [18] A. Urtti, Z. Hyvonen, A. Plotniece, N. Makarova, I. Reine, G. Tirzitis, B. Vigante, B. Cekavicus, A. Shmidlers, A. Krauze, R. Zhalubovskis, G. Duburs, M. Turunen, S. Yla-Herttuala, I. Jaaskelainen, M.R. Toppinen, WO 01/62946 A1, 2001; Chem. Abstr. 135, 206419h (2001)
  • [19] N. Makarova, G. Belevich, E. Bisenieks, M. Veveris, G. Dubur, Pharm. Chem. J. 22, 534 (1988) http://dx.doi.org/10.1007/BF00763523[Crossref]
  • [20] B. B. Subudhi, P. K. Panda, B. Bhatta, Indian J. Chem. B. Org. 48B, 725 (2009)
  • [21] M. Filipan-Litvic, M. Litvic, V. Vinkovic, Bioorg. Med. Chem. 16, 9276 (2008) http://dx.doi.org/10.1016/j.bmc.2008.09.004[Crossref]
  • [22] A.R. Bader, L.O. Cummings, H.A. Vogel, J. Am. Chem. Soc. 73, 4195 (1951) http://dx.doi.org/10.1021/ja01153a045[Crossref]
  • [23] R.O. Robin, W. Moore, US Patent 2305558, 1942; Chem. Abstr. 37, P32201 (1943)
  • [24] M. Suarez, M. De Armas, O. Ramırez, A. Alvarez, R.M. Alvarez, D. Molero, C. Seoane, R. Liz, H.N. De Armas, N.M. Blaton, O.M. Peeters, N. Martın, New J. Chem. 29, 1567 (2005) http://dx.doi.org/10.1039/b506018d[Crossref]
  • [25] E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, F. Shirini, M.A. Zolfigol, J. Iran. Chem. Soc. 4, 126 (2007) [Crossref]
  • [26] I.P. Skrastinsh, V.V. Kastron, B.S. Chekavichus, A.E. Sausinsh, R.M. Zolotoyabko, G.Y. Dubur, Khim. Geterotsikl. Soedin. 1230 (1991) [Chem. Heterocycl. Comp. 27, 989 (1991)]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-010-0132-x
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.