PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2014 | 12 | 1 | 115-125
Article title

Novel ion-binding C3 symmetric tripodal triazoles: synthesis and characterization

Content
Title variants
Languages of publication
EN
Abstracts
EN
Novel C3 symmetric tripodal molecules were synthesized from cyclohexane 1,3,5-tricarboxylic acid. Utilizing click and Sonogashira reactions, ion-binding triazole and pyridazin-3(2H)-one units were incorporated to form polydentate ligands for ion complexation. The structures of the novel C3 symmetric derivatives were extensively characterized by 1H, 13C and 2D NMR techniques along with HRMS and IR. The copper(I)-binding potentials of these ligands were investigated by using them as additives in model copper(I)-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The copper(I) complexation ability of our compound was also proved by different spectroscopic methods, such as mass spectrometry, UV and NMR spectroscopy. Based on the mass spectrometric data all of the C3 symmetric ligands formed 1:1 complex with copper(I) ion. The specific role of C3 symmetric polydentate form in the complexation process was also discussed [...]
Publisher

Journal
Year
Volume
12
Issue
1
Pages
115-125
Physical description
Dates
published
1 - 1 - 2014
online
27 - 10 - 2013
References
  • [1] A.M. Pujol, C. Gateau, C. Lebrun, P. Delangle, J. Am. Chem. Soc. 131, 6928 (2009) http://dx.doi.org/10.1021/ja901700a[Crossref]
  • [2] B. Pedras, E. Oliveira, H. Santos, L. Rodríguez, R. Crehuet, T. Avilés, J.L. Capelo, C. Lodeiro, Inor. Chim. Acta 362, 2627 (2009) http://dx.doi.org/10.1016/j.ica.2008.11.032[Crossref]
  • [3] S.G. Tajc, B.L. Miller, J. Am. Chem. Soc. 128, 2532 (2006) http://dx.doi.org/10.1021/ja058126p[Crossref]
  • [4] N. Kaur, N. Singh, D. Cairns, J.F. Callan, Org. Lett. 11, 2229 (2009) http://dx.doi.org/10.1021/ol900388x[Crossref]
  • [5] A. Baschieri, A. Mazzanti, S. Stagni, L. Sambri, Eur. J. Inorg. Chem. 2432 (2013)
  • [6] D.Y. Lee, N. Singh, M.J. Kim, D.O. Jang, Org. Lett. 13, 3024 (2011) http://dx.doi.org/10.1021/ol2008846[Crossref]
  • [7] M. Arunachalam, P. Ghosh, Org. Lett. 12, 328 (2010) http://dx.doi.org/10.1021/ol9026649[Crossref]
  • [8] K. Murai, S. Fukushima, S. Hayashi, Y. Takahara, H. Fujioka, Org. Lett. 12, 964 (2010) http://dx.doi.org/10.1021/ol902958m[Crossref]
  • [9] D. Wang, X. Zhang, C. He, C. Duan, Org. Biomol. Chem. 8, 2923 (2010) http://dx.doi.org/10.1039/c004148c[Crossref]
  • [10] X.-L. Ni, S. Wang, T. Yamato, X. Zeng, Z. Tao, Org. Lett. 13, 552 (2011) http://dx.doi.org/10.1021/ol102914t[Crossref]
  • [11] D. Wynn, I.M. Newington, WO 133090 Patent (2007)
  • [12] R. Huisgen, Proc. Chem. Soc. 357 (1961)
  • [13] R. Huisgen, Angew. Chem. Int. Ed. 2, 565 (1963) http://dx.doi.org/10.1002/anie.196305651[Crossref]
  • [14] C.W. Tornøe, C. Christensen, M.J. Meldal, Org. Chem. 67, 3057 (2002) http://dx.doi.org/10.1021/jo011148j[Crossref]
  • [15] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002) http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4[Crossref]
  • [16] S. Díez-González, A. Correa, L. Cavallo, S.P. Nolan, Chem. Eur. J. 12, 7558 (2006) http://dx.doi.org/10.1002/chem.200600961[Crossref]
  • [17] N. Candelon, D. Lastécouères, A.K. Diallo, J.R. Aranzaes, D. Astruc, J.-M. Vincent, Chem. Commun. 741 (2008)
  • [18] T.R. Chan, R. Hilgraf, K.B. Sharpless, V.V. Fokin, Org. Lett. 6, 2853 (2004) http://dx.doi.org/10.1021/ol0493094[Crossref]
  • [19] L. Zhang, X. Chen, P. Xue, H.H.Y. Sun, I.D. Williams, K.B. Sharpless, V.V. Fokin, G. Jia, J. Am. Chem. Soc. 127, 15998 (2005) http://dx.doi.org/10.1021/ja054114s[Crossref]
  • [20] M.-H. Ryu, J.-W. Choi, B.-K. Cho, H.-J. Kim, N. Park, Angew. Chem. Int. Ed. 50, 5737 (2011) http://dx.doi.org/10.1002/anie.201101013[Crossref]
  • [21] J.W. Lee, J.H. Kim, B.-K. Kim, W.S. Shin, S.-H. Jin, Tetrahedron 62, 894 (2006) http://dx.doi.org/10.1016/j.tet.2005.10.039[Crossref]
  • [22] A. Ustinov, H. Weissman, E. Shirman, I. Pinkas, X. Zuo, B. Rybtchinski, J. Am. Chem. Soc. 133, 16201 (2011) http://dx.doi.org/10.1021/ja2066225[Crossref]
  • [23] J.E. Moses, D.J. Ritson, F. Zhang, N. Oldham, C.M. Lombardo, S. Haider, S. Neidle, Org. Biomol. Chem. 8, 2926 (2010) http://dx.doi.org/10.1039/c005055e[Crossref]
  • [24] E. Beltrán, J.L. Serrano, T. Sierra, R. Giménez, Org. Lett. 12, 1404 (2010) http://dx.doi.org/10.1021/ol902900y[Crossref]
  • [25] D.M. Zink, S. Braese, T. Baumann, M. Nieger, Eur. J. Org. Chem. 1432 (2011) [Crossref]
  • [26] M.R. Krause, S. Kubik, R.J. Goddard, Org. Chem. 76, 7084 (2011) http://dx.doi.org/10.1021/jo201024r[Crossref]
  • [27] X.-L. Ni, T. Yamato, X. Zeng, C.J. Redshaw, Org. Chem. 76, 5696 (2011) http://dx.doi.org/10.1021/jo2007303[Crossref]
  • [28] A. Coelho, E. Sotelo, H. Novoa, O.M. Peeters, N. Blaton, E. Raviña, Tetrahedron 60, 12177 (2004) http://dx.doi.org/10.1016/j.tet.2004.10.014[Crossref]
  • [29] B.C. Boren, S. Narayan, L.K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V.V. Fokin, J. Am. Chem. Soc. 130, 8923 (2008) http://dx.doi.org/10.1021/ja0749993[Crossref]
  • [30] Zs. Gonda, Z. Novák, Dalton Trans. 39, 726 (2010) http://dx.doi.org/10.1039/b920790m[Crossref]
  • [31] Sz. Kovács, K. Zih-Perényi, Z. Novák, Á. Révész, Synthesis 44, 3722 (2012) http://dx.doi.org/10.1055/s-0032-1317697[Crossref]
  • [32] H.A. Stefani, H.A. Canduzini, F. Manarin, Tetrahedron Lett. 52, 6086 (2011) http://dx.doi.org/10.1016/j.tetlet.2011.09.004[Crossref]
  • [33] P. Kele, X. Li, M. Link, K. Nagy, A. Herner, K. Lőrincz, Sz. Béni, O.S. Wolfbeis, Org. Biomol. Chem. 7, 3486 (2009) http://dx.doi.org/10.1039/b907741c[Crossref]
  • [34] A.V. Moro, P.C. Ferreira, P. Migowski, F.S. Rodembusch, J. Dupont, D.S. Lüdtke, Tetrahedron, 69, 201 (2013) http://dx.doi.org/10.1016/j.tet.2012.10.043[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-013-0351-z
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.