Cu-catalyzed N-alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 980-983

  Burley, Glenn A ^a   Davies, David L ^a   Griffith, Gerry A ^a   Lee, Michael ^a   Singh, Kuldip ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATIONS; ALKYNYLS; BENZIMIDAZOLES; CHEMICAL EQUATIONS; CROSS-COUPLINGS; HETEROARENES; INDAZOLE; PEG-400; PHASE TRANSFER; PYRAZOLES; STABILIZING LIGANDS;

ETHYLENE; ETHYLENE GLYCOL; FUNCTIONAL GROUPS; MICROWAVE IRRADIATION; PLANTS (BOTANY); POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES;

CHEMICAL REACTIONS;

ALKYNE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BROMOALKYNE DERIVATIVE; COPPER; IMIDAZOLE DERIVATIVE; INDAZOLE DERIVATIVE; MACROGOL 400; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALKYNYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; HYDROGEN BOND; MICROWAVE IRRADIATION; SUBSTITUTION REACTION;

EID: 75749107815     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902466f     Document Type: Article

References (29)

1. Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
2. Ishihara, T.; Mantani, T.; Konno, T.; Yamanaka, H. Tetrahedron 2006, 62, 3783.
3. Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett. 2003, 1379.
4. Xu, Z. Q.; Joshi, R. V.; Zemlicka, J. Tetrahedron 1995, 51, 67.
5. (a) Xu, Z. Q.; Joshi, R. V.; Zemlicka, J. Tetrahedron 1995, 51, 67.
6. (b) Joshi, R. V.; Xu, Z. Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089.
7. Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381.
8. (a) Altman, R. A.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2008, 73, 5167.
9. (b) Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190.
10. (c) Altman, R. A.; Buchwald, S. L. Org. Lett. 2007, 9, 643.
11. (d) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
12. (a) Yao, P. Y.; Zhang, Y.; Hsung, R. P.; Zhao, K. Org. Lett. 2008, 10, 4275.
13. (b) Zhang, X. J.; Zhang,Y. S.;Huang, J.;Hsung,R. P.;Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L. C.; Tracey, M.R. J. Org.Chem. 2006, 71, 4170.
14. (c)Zhang,Y.; Hsung, R. P.;Tracey,M.R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6 (7), 1151-1154.
15. Laroche, C.; Li, J.; Freyer, M. W.; Kerwin, S. M. J. Org. Chem. 2008, 73, 6462.
16. (a) Gao, Y. X.; Wang, G.; Chen, L.; Xu, P. X.; Zhao, Y. F.; Zhou, Y. B.; Han, L. B. J. Am. Chem. Soc. 2009, 131, 7956.
17. (b) Evano, G.; Toumi, M.; Coste, A. Chem. Commun. 2009, 4166.
18. (c) de Parrodi, C. A.; Walsh, P. J. Angew. Chem., Int. Ed. 2009, 48, 4679.
19. Strieter, E. R.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 78.
20. Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
21. (a) She, J.; Jiang, Z.; Wang, Y. Tetrahedron Lett. 2009, 50, 593.
22. (b) Mao, J. C.; Guo, J.; Fang, F. B.; Ji, S. J. Tetrahedron 2008, 64, 3905.
23. (c) Wang, L. A.; Zhang, Y. H.; Liu, L. F.; Wang, Y. G. J. Org. Chem. 2006, 71, 1284.
24. 3 (54 mg, 0.17 mmol). A solution of PEG400 (50 mg) in dioxane (0.5 mL) was added, and the reaction mixture evacuated and back filled with argon. The reaction mixture was then heated under microwave irradiation (125 W) at 85 °Cfor 60 min.GC-MSanalysis observed only starting material present in the crude mixture.
25. For a recent example of π-activation of an alkyne by copper, see: Laroche, C.; Kerwin, S. M. J. Org. Chem. 2009, 74, 9229-9232.
26. The United Kingdom Chemical Database Service; Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comp. Sci. 1996, 36, 746.
27. Li, J.; Kaoud, T. S.; Laroche, C.; Dalby, K. N.; Kerwin, S.M. Bioorg. Med. Chem. Lett. 2009, 19 (22), 6293-6297.
28. Tracey, M. R.; Zhang, Y. S.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209.
29. Brown, R. F. C.; Eastwood, F. W.; Fallon, G. D.; Lee, S. C.; McGeary, R. P. Aust. J. Chem. 1994, 47, 991.