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

• Autorzy: Karlis Pajuste , Aiva Plotniece , Kintija Kore , Liva Intenberga , Brigita Cekavicus , Dainis Kaldre , Gunars Duburs , Arkadij Sobolev
• Języki publikacji: EN

Abstrakty

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. [...]

Słowa kluczowe

EN

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

• Czasopismo: Open Chemistry
• Rocznik: 2011
• Tom: 9
• Numer: 1
• Strony: 143-148

Daty

wydano

2011-02-01

online

2010-12-16

Twórcy

autor

Karlis Pajuste

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

autor

Aiva Plotniece

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

autor

Kintija Kore

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

autor

Liva Intenberga

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

autor

Brigita Cekavicus

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

autor

Dainis Kaldre

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

autor

Gunars Duburs

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

autor

Arkadij Sobolev

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

Bibliografia

• [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)]

Identyfikatory

DOI

10.2478/s11532-010-0132-x