Efficient route to hybrid polypyridine-carboxylate ligands for lanthanide complexation

Tetrahedron Letters

Volumn 48, Issue 52, 2007, Pages 9132-9136

  Mameri, Samir ^a   Charbonnière, Loïc ^a   Ziessel, Raymond ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOBUTYL BROMO TERPYRIDINE; CARBOXYLIC ACID; IMINE; LANTHANIDE; LIGAND; POLYPYRIDINE; PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROLYSIS; LUMINESCENCE; SPECTROSCOPY; SYNTHESIS;

EID: 36549038039     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.121     Document Type: Article

References (33)

1. Erkkila K.E., Odom D.T., and Barton J.K. Chem. Rev. 99 (1999) 2777
2. Barigelletti F., and Flamigni L. Chem. Soc. Rev. 29 (2000) 1
3. Hofmeier H., and Schubert U.S. Chem. Soc. Rev. 33 (2004) 373
4. Harriman A., Rostron S.A., Khatyr A., and Ziessel R. Faraday Discuss. 131 (2006) 377
5. Slinker J., Bernards D., Houston P.L., Abruna H.D., Berhard S., and Malliaras G.G. Chem. Commun. (2003) 2392
6. Montes V.A., Perz-Bolivar C., Agarwal N., Shinar J., and Anzenbacher Jr. P. J. Am. Chem. Soc. 128 (2006) 12436
7. Harriman A., and Ziessel R. In: Haley M.M., and Tykwinski R.R. (Eds). Carbon-Rich Compounds from Molecules to Materials (2006), Wiley-VCH, Weiheim 26-89
8. de Bettencourt-Dias A.J. Dalton Trans. (2007) 2229
9. Beeby A., Clarkson I.M., Dickins R.S., Faulkner S., Parker D., Royle L., de Sousa A.S., Williams J.A.G., and Woods M. J. Chem. Soc., Perkin Trans. 2 (1999) 493
10. Hasegawa Y., Wada Y., and Yanagida S. J. Photochem. Photobiol. C 5 (2004) 183
11. Brunet E., Juanes O., and Rodriguez-Ubis J.-C. Curr. Chem. Biol. 1 (2007) 11
12. Bünzli J.-C.G., and Piguet C. Chem. Soc. Rev. 34 (2005) 1048
13. Charbonnière L., Hildebrandt N., Ziessel R., and Löhmannsröben H.-G. J. Am. Chem. Soc. 128 (2006) 12800
14. Hemmilä I., and Webb S. Drug Discovery Today 2 (1997) 373
15. Caravan P., Ellison J.J., Mc Murry T.J., and Lauffer R.B. Chem. Rev. 99 (1999) 2293
16. Charbonnière L., Ziessel R., Guardigli M., Roda A., Sabbatini N., and Cesario M. J. Am. Chem. Soc. 123 (2001) 2436
17. Weibel N., Charbonnière L.J., Guardigli M., Roda A., and Ziessel R. J. Am. Chem. Soc. 126 (2004) 4888
18. Latva M., Takalo H., Mukkala V.-M., Matachescu C., Rodriguez-Ubis J.C., and Kankare J. J. Lumin. 75 (1997) 149
19. Bretonnière Y., Mazzanti M., Pécaut J., and Olmstead M.M. J. Am. Chem. Soc. 124 (2002) 9012
20. Compound 1 was obtained in 36% yield by radical bromination of ethyl 6-methyl-2-picolinate (Singh, K.; Long, J.R.; Stavropoulos, P. Inorg. Chem. 1998, 37, 1073) using NBS in refluxing benzene for 2 h with AIBN (cat.) and a 100 W halogen lamp as heating source.
21. Mameri S., Charbonnière L., and Ziessel R. Synthesis 17 (2003) 2713
22. Charbonnière L.J., Mameri S., Flot D., Waltz F., Zandanel C., and Ziessel R. Dalton Trans. (2007) 2245
23. Weibel N., Charbonnière L.J., and Ziessel R. J. Org. Chem. 67 (2002) 7876
24. El Ghayoury A., and Ziessel R. J. Org. Chem. 65 (2000) 7757
25. Weibel N., Charbonnière L., and Ziessel R. Tetrahedron Lett. 47 (2006) 1793
26. 2O: C, 55.99; H, 5.19; N, 12.03. Found: C, 56.19; H, 5.05; N, 11.92.
27. Penicaud V., Odobel F., and Bujoli B. Tetrahedron Lett. 39 (1998) 3689
28. 2O: C, 43.73; H, 4.22; N, 10.20. Found: C, 44.28; H, 4.62; N, 10.19.
29. Prodi L., Montali M., Zaccheroni N., Pickaert G., Charbonnière L., and Ziessel R. New J. Chem. 27 (2003) 134
30. 2O: C, 51.21; H, 4.18; N, 11.00. Found: C, 51.09; H, 4.01; N, 10.73.
31. Supkowski R.M., and Horrocks Jr. W.D.W. Inorg. Chim. Acta 340 (2002) 44
32. Chatterton N., Bretonnière Y., Pécaut J., and Mazzanti M. Angew. Chem., Int. Ed. 44 (2005) 7595
33. Charbonnière, L.; Mameri, S.; Kadjane, P.; Platas-Iglesias, C.; Ziessel, R., unpublished results.