Abstract
Selective and high yield synthesis of N-substituted salicylic acid derivatives of cyclen has been achieved by using a direct synthetic procedure under mild reaction conditions. The protonation constants of these compounds were determined by potentiometric titration. The complexing properties of the cyclen derivatives with metal cations were investigated by UV–Vis spectroscopy and 1H NMR. The stability constants of Mg2+, Ca2+ and Sr2+ complexes with ligands 5 and 6 were determined.
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Zahang S., Sherry D.A., (2003). J. Solid State Chem. 171: 38
Bennur T.H., Srinivas D., Sivasanker S., (2004). J. Mol. Catal. A Chem. 207: 163
Gunnlaugsson T., Davies R.J.H., Nieuwenhuyzen M., O’Brien J.E., Stevenson C.S., Mulready M., (2003) Polyhedron 22: 711
Kim D.H., Han M.S., (2003). Bioorg. Med. Chem. Lett. 13: 2543
(a) D. Parker, R.S. Dickins, H. Puschmann, C. Crossland, and J.A.K. Howard: Chem. Rev. 102, 1977 (2002); (b) D. Maffeo and J.A.G. Williams: Inorg. Chem. Acta 355, 127 (2003)
(a) R. Ziessel, M. Hissler, and G. Ulrich: Synthesis 9, 1339 (1998); (b) H.C. Freake and Ch. Brücker: Bioorg. Med. Chem. Lett. 13, 2251 (2003)
(a) L.H.J. Lajunen, R. Portanova, R.J. Piispanen, and M. Tolazz: Pure Appl. Chem. 69(2), 329 (1997); (b) M. Terezia, E.A. Suranyi, A. Djurendic, and G.G. Vastag: Collec. Czech. Chem. Commun. 60(3), 464 (1995)
Kasibhatla S.R., Bokser B.C., Probst G., Appleman J.R., Erion M.D., (2000). J. Med. Chem. 43: 1508
Augstein J., Austin W.C., Boscott R.J., Green S.M., Worthing C.R., (1965) J. Med. Chem. 8: 356
(a) E. Kiura, S. Aoki, T. Koike, and M. Shiro: J. Am. Chem. Soc. 119, 3068 (1997); (b) D.D. Dischino, E.J. Delaney, J.E. Emswiler, G.T. Gaughan, J.S. Prasad, S.K. Srivastava, and M.F. Tweedle: Inorg. Chem. 30, 1265 (1991); (c) V. Boldrini, G.B. Giovenzana, R.␣Pagliarin, G. Palmisano, and M. Sisty: Tetrahedron Lett. 41, 6527 (2000)
(a) I.M. Helps, D. Parker, J.R. Morphy, and J. Chapman: Tetrahedron 45, 219 (1989); (b) C. Li and W.T. Wong: Tetrahedron Lett. 43, 3217 (2002)
Skwierawska A., Paluszkiewicz E., Przyborowska M., Ossowski T., (2004). J. Incl. Plenom. Macrocyc. Chem. 49: 21
Koike T., Kajitani S., Nakamura I., Kiura E., Shiro M., (1995). J. Am. Chem. Soc. 117: 1210
Acknowledgements
We gratefully acknowledge financial support from the DS No. 014668/003. The authors indebted to Professor J.F. Biernat for valuable discussion and assistance in preparation in this manuscript.
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Skwierawska, A.M., Paluszkiewicz, E. High Yield Synthesis and Preliminary Spectroscopic Study of Mono-N-alkylated Cyclen Derivatives of Salicylic Acid . J Incl Phenom Macrocycl Chem 56, 323–330 (2006). https://doi.org/10.1007/s10847-006-9101-6
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DOI: https://doi.org/10.1007/s10847-006-9101-6