Novel tetradentate chelators derived from 3-hydroxy-4-pyridinone units: Synthesis, characterization and aqueous solution properties

Tetrahedron

Volumn 67, Issue 22, 2011, Pages 4009-4016

  Leite, Andreia ^a   Silva, Ana M G ^a   Nunes, Ana ^a   Andrade, Mariana ^a   Sousa, Carla ^b   Cunha Silva, Luís ^a   Gameiro, Paula ^a   De Castro, Baltazar ^a   Rangel, Maria ^c  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSIDADE FERNANDO PESSOA   (Portugal)

^c Campus Universitário de Santiago   (Portugal)

Author keywords

3 Hydroxy 4 pyridinone ligands; Acid base properties; Tetradentate chelators

Indexed keywords

1,2 PHENYLENEDIAMINE; 3 HYDROXY 4 PYRIDINONE; BENZENE DERIVATIVE; CHELATING AGENT; COPPER ION; HYDROGEN; PIPERAZINE; PROTON; PYRIDONE DERIVATIVE; TETRADENTATE 1 LIGAND; TETRADENTATE 2 LIGAND; TETRADENTATE 3 LIGAND; UNCLASSIFIED DRUG; ZINC ION;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEATING; HYDROGEN BOND; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETRY; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 79955794728     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.035     Document Type: Article

References (45)

1. B. Burgess, and M. Rangel Adv. Inorg. Chem. 60 2008 167
2. M.A. Santos Coord. Chem. Rev. 252 2008 1213
3. A. Nunes, M. Podinovskaia, A. Leite, P. Gameiro, T. Zhou, Y. Ma, X. Kong, U.E. Schaible, R.C. Hider, and M. Rangel J. Biol. Inorg. Chem. 15 2010 861
4. Y.M. Ma, and R.C. Hider Bioorg. Med. Chem. 17 2009 8093
5. M.A. Esteves, A. Cachudo, S. Chaves, and M.A. Santos Eur. J. Inorg. Chem. 2005 597 605
6. J.M. Harrington, S. Chittamuru, S. Dhungana, H.K. Jacobs, A.S. Gopalan, and A.L. Crumbliss Inorg. Chem. 49 2010 8208
7. T.N. Lambert, S. Chittamuru, H.K. Jacobs, and A.S. Gopalan Tetrahedron Lett. 43 2002 7379
8. L. Tei, Z. Baranyai, E. Brücher, C. Cassino, F. Demicheli, N. Masciocchi, G.B. Giovenzana, and M. Botta Inorg. Chem. 49 2010 616
9. Y. Niu, H. Hou, Y. Wei, Y. Fan, Y. Zhu, C. Du, and X. Xin Inorg. Chem. Commun. 4 2001 358
10. G. Li, J. Lü, X. Li, H. Yang, B. Xu, and R. Cao CrystEngComm 12 2010 3780
11. S.-C. Hsu, J.-Y. Wu, C.-F. Lee, C.-C. Lee, L.-L. Lai, and K.-L. Lu CrystEngComm 12 2010 3388
12. S. Chaves, S.M. Marques, A.M.F. Matos, A. Nunes, L. Gano, T. Tuccinardi, A. Martinelli, and M.A. Santos Chem. - Eur. J. 16 2010 10535
13. For microwave heating reviews see: S. Caddick, and R. Fitzmaurice Tetrahedron 65 2009 3325
14. C.O. Kappe, and D. Dallinger Mol. Divers. 13 2009 71
15. V. Polshettiwar, and R.S. Varma Chem. Soc. Rev. 37 2008 1546
16. C.O. Kappe Chem. Soc. Rev. 37 2008 1127
17. D. Dallinger, and C.O. Kappe Chem. Rev. 127 2007 2563
18. M. Nüchter, B. Ondruschka, W. Bonrath, and A. Gum Green Chem. 6 2004 128
19. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250
20. For recent examples see: B. Di Credico, G. Reginato, L. Gonsalvi, M. Peruzzini, and A. Rossin Tetrahedron 67 2011 267
21. A.M.G. Silva, A. Leite, M. Andrade, P. Gameiro, P. Brandão, V. Felix, B. de Castro, and M. Rangel Tetrahedron 66 2010 8544
22. D. Tang, J.R. Buck, M.R. Hight, and H.C. Manning Tetrahedron Lett. 51 2010 4595
23. A. Allam, J.-B. Behr, L. Dupont, V. Nardello-Rataj, and R. Plantier-Royon Carbohydr. Res. 345 2010 731
24. S.-H. Zhang, and C. Feng J. Mol. Struct. 977 2010 62
25. Y.S. Lee, S. Fernandes, V. Kulkarani, A. Mayorov, P. Davis, S.-w. Ma, K. Brown, R.J. Gillies, J. Lai, F. Porreca, and V.J. Hruby Bioorg. Med. Chem. Lett. 20 2010 4080
26. G. Farruggia, S. Iotti, M. Lombardo, C. Marraccini, D. Petruzziello, L. Prodi, M. Sgarzi, C. Trombini, and N. Zaccheroni J. Org. Chem. 75 2010 6275
27. A. Goldys, and C.S.P. McErlean Tetrahedron Lett. 50 2009 3985
28. L.C.F. Pimentel, A.L.F. de Souza, T.L. Fernández, J.L. Wardella, and O.A.C. Antunes Tetrahedron Lett. 48 2007 831
29. Z. Dega-Szafran, M. Jaskólski, I. Kurzyca, P. Barczyński, and M. Szafran J. Mol. Struct. 614 2002 23
30. C. Queiros, M.J. Amorim, A. Leite, M. Ferreira, P. Gameiro, B. de Castro, K. Biernacki, A. Magalhães, J. Burgess, and M. Rangel Eur. J. Inorg. Chem. 2011 131
31. M. Rangel, A. Leite, M.J. Amorim, E. Garriba, G. Micera, and E. Lodyga-Chruscinska Inorg. Chem. 45 2006 8086
32. L. Li, N.N. Murthy, J. Telser, L.N. Zakharov, G.P.A. Yap, A.L. Rheingold, K.D. Karlin, and S.E. Rokita Inorg. Chem. 45 2006 7144
33. M.A. Santos, M. Gil, S. Marques, L. Gano, G. Cantinho, and S. Chaves J. Inorg. Biochem. 92 2002 43
34. T. Kottke, and D. Stalke J. Appl. Crystallogr. 26 1993 615 619
35. APEX2. Data Collection Software Version 2.1-RC13 2006 Bruker AXS Delft, The Netherlands
36. Cryopad. Remote Monitoring and Control, Version 1.451 2006 Oxford Cryosystems Oxford, United Kingdom
37. © 1997-2005 Bruker AXS Madison, WI, USA
38. G.M. Sheldrick SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program 1998 Bruker AXS Madison, WI, USA
39. G.M. Sheldrick Acta Crystallogr. A 64 2008 112 122
40. G.M. Sheldrick SHELXS-97, Program for Crystal Structure Solution 1997 University of Göttingen Göttingen
41. G.M. Sheldrick SHELXL-97, Program for Crystal Structure Refinement 1997 University of Göttingen Göttingen
42. G. Gran Analyst 77 1952 661 671
43. F. Rossotti, and H. Rossotti J. Chem. Educ. 42 1965 375
44. P. Gans, A. Sabatini, and A. Vacca Talanta 43 1996 1739
45. A. Albert, and E.P. Sergeant The Determination of Ionization Constants 2nd ed. 1971 Chapman & Hall London