Unexpected product distributions in the synthesis of 2,6-bis-(indazolyl)pyridine and 2-(pyrazol-1-yl)-6-(indazolyl)pyridine

Tetrahedron Letters

Volumn 50, Issue 21, 2009, Pages 2484-2486

  Pritchard, Ruth ^a   Kilner, Colin A ^a   Halcrow, Malcolm A ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Crystal structure; Indazolylpyridines; Nucleophilic substitution; Regiochemistry

Indexed keywords

2 (INDAZOL 1 YL) 6 (INDAZOL 1 YL)PYRIDINE; 2 (INDAZOL 1 YL) 6 BROMOPYRIDINE; 2 (INDAZOL 2 YL) 6 BROMOPYRIDINE; 2 (PYRAZOL 1 YL) 6 (INDAZOL 1 YL)PYRIDINE; 2 (PYRAZOL 1 YL) 6 (INDAZOLYL)PYRIDINE; 2 (PYRAZOL 1 YL) 6 BROMOPYRIDINE; 2 BROMOPYRIDINE; 2,6 BIS INDAZOLYLPYRIDINE; 2,6 BIS(INDAZOL 1 YL)PYRIDINE; 2,6 BIS(INDAZOL 1 YL)PYRIDINE AND 2 (INDAZOL 1 YL) 6 (INDAZOL 2 YL)PYRIDINE; 2,6 DI(PYRAZOL 1 YL)PYRIDINE; DIGLYME; IRON; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 63749099267     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.035     Document Type: Article

References (32)

1. Halcrow M.A. Coord. Chem. Rev. 249 (2005) 2880 and references therein
2. Gütlich, P.; Goodwin, H. A.; Eds., Spin Crossover in Transition Metal Compounds I-III, Top. Curr. Chem.; 2004, pp 233-235.
3. Gütlich P., van Koningsbruggen P.J., and Renz F. Struct. Bond. (Berlin) 107 (2004) 27
4. Real J.A., Gaspar A.B., and Muñoz M.C. Dalton Trans. (2005) 2062
5. Sato O., Tao J., and Zhang Y.-Z. Angew. Chem., Int. Ed. 46 (2007) 2152
6. Halcrow M.A. Chem. Soc. Rev. 37 (2008) 278
7. Carbonera C., Costa J.S., Money V.A., Elhaïk J., Howard J.A.K., Halcrow M.A., and Létard J.-F. Dalton Trans. (2006) 3058
8. Money V.A., Carbonera C., Elhaïk J., Halcrow M.A., Howard J.A.K., and Létard J.-F. Chem. Eur. J. 13 (2007) 5503
9. Pritchard R., Kilner C.A., and Halcrow M.A. Chem. Commun. (2007) 577
10. Carbonera C., Kilner C.A., Létard J.-F., and Halcrow M.A. Dalton Trans. (2007) 1284
11. Elhaïk J., Pask C.M., Kilner C.A., and Halcrow M.A. Tetrahedron 63 (2007) 291
12. Han L., Nihei M., and Oshio H. Polyhedron 24 (2005) 2409
13. Nihei M., Han L., and Oshio H. J. Am. Chem. Soc. 129 (2007) 5312
14. Nihei M., Maeshima T., Kose Y., and Oshio H. Polyhedron 26 (2007) 1993
15. Rajadurai C., Schramm F., Brink S., Fuhr O., Ghafari M., Kruk R., and Ruben M. Inorg. Chem. 45 (2006) 10019
16. Rajadurai C., Fuhr O., Kruk R., Ghafari M., Hahn H., and Ruben M. Chem. Commun. (2007) 2636
17. Rajadurai C., Qu Z., Fuhr O., Gopalan B., Kruk R., Ghafari M., and Ruben M. Dalton Trans. (2007) 3531
18. Chandrasekar R., Schramm F., Fuhr O., and Ruben M. Eur. J. Inorg. Chem. (2008) 2649
19. Matsuda M., and Tajima H. Chem. Lett. (2007) 700
20. Matsuda M., Isozaki H., and Tajima H. Chem. Lett. (2008) 374
21. See, for example:. Boča R., Boča M., Dlháň L., Falk K., Fuess H., Haase W., Jaroščiak R., Papánková B., Renz F., Vrbová M., and Werner R. Inorg. Chem. 40 (2001) 3025 and references therein
22. Zaidi S.A.A., Shahjahan M., and Siddiqui K.S. Transition Met. Chem. 18 (1993) 51
23. Chan D.M.T., Monaco K.L., Li R., Bonne D., Clark C.G., and Lam P.Y.S. Tetrahedron Lett. 44 (2003) 3863
24. Jameson D.L., and Goldsby K.A. J. Org. Chem. 55 (1990) 4992
25. Palladium catalysis of this reaction leads to reduced reaction times, but with no significant increase in yield or product purity. See:. Sun X., Yu Z., Wu S., and Xiao W.-J. Organometallics 24 (2005) 2959
26. Begtrup M., Claramunt R.M., and Elguero J. J. Chem. Soc., Perkin Trans. 2 (1978) 99
27. Palmer M.H., Findlay R.H., Kennedy S.M.F., and McIntyre P.S. J. Chem. Soc., Perkin Trans. 2 (1975) 1695
28. Claramunt R.M., Elguero J., and Garceran R. Heterocycles 23 (1985) 2895
29. Isin E.M., de Jonge M., and Castagnoli N. J. Org. Chem. 66 (2001) 4220
30. Luo G., Chen L., and Dubowchik G. J. Org. Chem. 71 (2006) 5392
31. - anions (four of them disordered); and several partially occupied nitromethane, diethyl ether and water sites. See Supplementary data for more detailed information. CCDC 713035.
32. Pauling L. The Nature of the Chemical Bond. 3rd ed. (1960), Cornell University, Ithaca NY, USA