A convenient synthesis of 6,6′-dimethyl-2,2′-bipyridine-4-ester and its application to the preparation of bifunctional lanthanide chelators

Tetrahedron Letters

Volumn 48, Issue 6, 2007, Pages 999-1002

  Havas, Fabien ^a   Danel, Mathieu ^a   Galaup, Chantal ^a   Tisnès, Pierre ^a   Picard, Claude ^a  

^a Universite Toulouse III Paul Sabatier   (France)

Author keywords

Bifunctional chelators; Bipyridine; Lanthanides

Indexed keywords

6,6' DIMETHYL 2,2' BIPYRIDINE 4 ESTER; CHELATING AGENT; ESTER DERIVATIVE; LANTHANIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; SYNTHESIS;

EID: 33846041339     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.012     Document Type: Article

References (37)

1. For a review, see:. Balzani V., Bergamini G., Marchioni F., and Ceroni P. Coord. Chem. Rev. 250 (2006) 1254-1266
2. Chelucci G., and Thummel R.P. Chem. Rev. 102 (2002) 3129-3170
3. Kaes C., Katz A., and Hosseini M.W. Chem. Rev. 100 (2000) 3553-3590
4. Sabbatini N., Guardigli M., and Lehn J.-M. Coord. Chem. Rev. 123 (1993) 201-228
5. Motson G.R., Fleming J.S., and Brooker S. Adv. Inorg. Chem. 55 (2004) 361-432
6. Hemmila I., and Mukkala V.-M. Crit. Rev. Clin. Lab. Sci. 38 (2001) 441-519
7. Faulkner S., Pope S.J.A., and Burton-Pye B.P. Appl. Spectrosc. Rev. 40 (2005) 1-31
8. Parker D. Coord. Chem. Rev. 205 (2000) 109-130
9. Cross J.P., Dadabhoy A., and Sammes P.G. J. Lumin. 110 (2004) 113-124
10. Couchet J.M., Galaup C., Tisnès P., and Picard C. Tetrahedron Lett. 44 (2003) 4869-4872
11. Galaup C., Azéma J., Tisnès P., Picard C., Ramos P., Juanes O., Brunet E., and Rodríguez-Ubis J.C. Helv. Chim. Acta 85 (2002) 1613-1625
12. Charbonnière L., Ziessel R., Guardigli M., Roda A., Sabbatini N., and Cesario M. J. Am. Chem. Soc. 123 (2001) 2436-2437
13. Galaup C., Carrié M.-C., Tisnès P., and Picard C. Eur. J. Org. Chem. (2001) 2165-2175
14. Mukkala V.-M., Kwiatkowski M., Kankare J., and Takalo H. Helv. Chim. Acta 76 (1993) 893-899
15. Bazin H., Trinquet E., and Mathis G. Rev. Mol. Biotech. 82 (2002) 233-250
16. Weibel N., Charbonnière L.J., Guardigli M., Roda A., and Ziessel R. J. Am. Chem. Soc. 126 (2004) 4888-4896
17. Bifunctional chelators (BFCs) are ligands that bear one end which is used to covalently attach the ligand to biological material and one end which strongly coordinates to the metallic ion; see for example:. Woods M., Kovacs Z., and Sherry A.D. J. Supramol. Chem. 2 (2002) 1-15
18. Picard C., Geum N., Nasso I., Mestre B., Tisnes P., Laurent S., Muller R.N., and Vander Elst L. Bioorg. Med. Chem. Lett. 16 (2006) 5309-5312
19. Nasso I., Galaup C., Havas F., Tisnès P., Picard C., Laurent S., Vander Elst L., and Muller R.N. Inorg. Chem. 44 (2005) 8293-8305
20. Lehn, J.-M.; Mathis, G.; Alpha, B.; Deschenaux, R.; Jolu, E. Eur. Patent 321,353, 1989.
21. Bedel, S. Ph.D., University Paul Sabatier, France, 2004.
22. Marvel C.S., and Dreger E.E. In: Blatt A.H. (Ed). Organic Syntheses Collective Vol. 1 (1941), Wiley, New York 238-240
23. Libermann D., Rist N., Grumbach F., Cals S., Moyeux M., and Rouaix A. Bull. Soc. Chim. Fr. (1958) 687-694
24. Cuiban, F.; Cilianu-Bibian, S.; Zaharescu, L. Fr Patent 1,362,967, 1964.
25. Stille-type coupling:. Schubert U.S., Eschbaumer C., and Heller M. Org. Lett. 2 (2000) 3373-3376
26. Hiyama-type coupling:. Hatanaka Y., and Hiyama T. J. Org. Chem. 53 (1988) 918-920
27. Fuerstner-type coupling:. Fürstner A., Leitner A., Méndez M., and Krause H. J. Am. Chem. Soc. 124 (2002) 13856-13863
28. Negishi-type coupling:. Negishi E. Acc. Chem. Res. 15 (1982) 340-348
29. Amat M., Hadida S., Pshenichnyi G., and Bosch J. J. Org. Chem. 62 (1997) 3158-3175
30. +, 100%].
31. Mathieu J., and Marsura A. Synth. Commun. 33 (2003) 409-414
32. Regnouf de Vains J.-B., Papet A.L., and Marsura A. J. Heterocycl. Chem. 31 (1994) 1069-1077
33. Galaup C., Couchet J.-M., Bedel S., Tisnès P., and Picard C. J. Org. Chem. 70 (2005) 2274-2284
34. Newkome G.R., Pappalardo S., Gupta V.K., and Fronczek F.R. J. Org. Chem. 48 (1983) 4848-4851
35. Rodriguez-Ubis J.C., Alpha B., Plancherel D., and Lehn J.-M. Helv. Chim. Acta 67 (1984) 2264-2269
36. 2O: C, 59.15; H, 4.70; N, 14.52. Found: C, 58.82; H, 4.89; N, 14.28.
37. D-0.25). 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) 493-503