2-Aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8324-8327

  Xie, Ye Xiang ^a   Pi, Shao Feng ^a   Wang, Jian ^a   Yin, Du Lin ^a   Li, Jin Heng ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-AMINOPYRIMIDINE-4,6-DIOL; HETEROARYL HALIDES; IMIDAZOLES;

CATALYST ACTIVITY; COPPER COMPOUNDS; NITROGEN COMPOUNDS;

AROMATIC POLYMERS;

2 AMINOPYRIMIDINE 4,6 DIOL; AMINOPYRIDINE DERIVATIVE; AMMONIUM FLUORIDE; COPPER BROMIDE; COPPER DERIVATIVE; HALIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; EVAPORATION; HIGH TEMPERATURE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALCOHOLS; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; IMIDAZOLES; LIGANDS; PYRIMIDINES;

EID: 33750033596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061572q     Document Type: Article

References (60)

1. For selected recent examples, see: (a) Zhong, C.; He, J.; Xue, C.; Li, Y. Bioorg. Med. Chem. 2004, 12, 4009.
2. (b) Dyck, B.; Goodfellow, V. S.; Phillips, T.; Grey, J.; Haddach, M.; Rowbottom, M.; Naeve, G. S.; Brown, B.; Saunders, J. Bioorg. Med. Chem. Lett. 2004, 14, 1151.
3. (c) Smallheer, J. M.; Alexander, R. S.; Wang, J.; Wang, S.; Nakajima, S.; Rossi, K. A.; Smallwod, A.; Barbera, F.; Burdick, D.; Luettgen, J. M.; Knabb, R. M.; Wexler, R. R.; Jadhav, P. K. Bioorg. Med. Chem. Lett. 2004, 14, 5263.
4. (d) Qiao, J. X.; Cheng, X.; Modi, D. P.; Rossi, K. A.; Luettgen, J. M.; Knabb, R. M.; Jadhav, P. K.; Wexler, R. R. Bioorg. Med. Chem. Lett. 2005, 15, 29.
5. (e) Mano, T.; Okumura, Y.; Sakakibara, M.; Okumura, T.; Tamura, T.; Miyamoto, K.; Stevens, R. W. J. Med. Chem. 2004, 47, 720.
6. (f) Roppe, J.; Smith, N. D.; Huang, D.; Tehrani, L.; Wang, B.; Anderson, J.; Brodkin, J.; Chung, J.; Jiang, X.; King, C.; Munoz, B.; Varney, M. A.; Prasit, P.; Cosford, N. D. P. J. Med. Chem. 2004, 47, 4645.
7. (g) Venkatesan, A. M.; Gu, Y.; Santos, O. D.; Abe, T.; Agarwal, A.; Yang, Y.; Petersen, P. J.; Weiss, W. J.; Mansour, T. S.; Nukaga, M.; Hujer, A. M.; Bonomo, R. A.; Knox, J. R. J. Med. Chem. 2004, 47, 6556.
8. (h) Lange, J. H. M.; van Stuivenberg, H. H.; Coolen, H. K. A. C.; Adolfs, T. J. P.; McCreary, A. C.; Keizer, H. G.; Wals, H. C.; Veerman, W.; Borst, A. J. M.; de Looff, W.; Verveer, P. C.; Kruse, C. G. J. Med. Chem. 2005, 48, 1823.
9. (i) Quan, M. L.; Lam, P. Y. S.; Han, Q.; Pinto, D. J. P.; He, M. Y.; Li, R.; Ellis, C. D.; Clark, C. G.; Teleha, C. A.; Sun, J.-H.; Alexander, R. S.; Bai, S.; Luettgen, J. M.; Knabb, R. M.; Wong, P. C.; Wexler, R. R. J. Med. Chem. 2005, 48, 1729.
10. (j) Barchéchath, S. D.; Tawatao, R. I.; Corr, M.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 2005, 48, 6409.
11. (k) Voets, M.; Antes, I.; Scherer, C.; Müller-Vieira, U.; Biemel, K.; Barassin, C.; Marchais-Oberwinkler, S.; Hartmann, R. W. J. Med. Chem. 2005, 48, 6632.
12. (l) Wiglenda, T.; Ott, I.; Kircher, B.; Schumacher, P.; Schuster, D.; Langer, T.; Gust, R. J. Med. Chem. 2005, 48, 6516.
13. (m) Jiang, W.; Guan, J.; Macielag, M. J.; Zhang, S.; Qiu, Y.; Kraft, P.; Bhattacharjee, S.; John, T. M.; Haynes-Johnson, D.; Lundeen, S.; Sui, Z. J. Med. Chem. 2005, 48, 2126.
14. For selected papers on the palladium-catalyzed N-arylations of imidazoles, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
15. (b) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 699.
16. (c) Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2005, 70, 3997.
17. For selected reviews on the use of copper as the catalyst, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
18. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
19. For a paper on the N-arylations of imidazoles with aryl halides mediated by stoichiometric copper, see: Lindley, J. Tetrahedron 1984, 40, 1433.
20. For papers on the copper-catalyzed N-arylations of imidazoles with aryl halides, see: (a) Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
21. (b) Kuil, M.; Bekedam, E. K.; Visser, G. M.; van den Hoogenband, A.; Terpstra, J. W.; Kamer, P. C. J.; Kamer van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Tetrahedron Lett. 2005, 46, 2405.
22. (c) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
23. (d) Kuil, M.; Bekedam, E. K.; Visser, G. M.; van den Hoogenband, A.; Terpstra, J. W.; Kamer, P. C.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Tetrahedron Lett. 2005, 46, 2405.
24. (e) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
25. (f) Alcalde, E.; Dinarès, I.; Rodríguez, S.; Garcia de Miguel, C. Eur. J. Org. Chem, 2005, 1637.
26. (g) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
27. (h) Jerphagnon, T.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. Org. Lett. 2005, 7, 5241.
28. (i) Ma, D.; Cai, Q. Synlett 2004, 128.
29. (j) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
30. (k) Lv, X.; Wang, Z.; Bao, W. Tetrahedron 2006, 62, 4756.
31. (l) Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135.
32. (m) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8107.
33. (n) Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553.
34. (o) Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435.
35. (p) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948.
36. (q) Son, S. U.; Park, I. K.; Park, J.; Hyeon, T. Chem. Commun. 2004, 778.
37. For selected representative papers on the copper-catalyzed N-arylations of imidazoles with other reagents, see: (a) Lopez-Alvarado, P.; Avendano, C.; Menéndez, J. C. J. Org. Chem. 1995, 60, 5678.
38. (b) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
39. (c) Collman, J. P.; Zhong, M.; Zeng, L.; Costanzo, S. J. Org. Chem. 2001, 66, 1528.
40. (d) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892.
41. (e) Lan, J.-B.; Chen, L.; Yu, X.-Q.; You, J.-S.; Xie, R.-G. Chem. Commun. 2004, 188.
42. (f) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
43. (g) Fedorov, A. Y.; Finet, J.-P. Tetrahedron Lett. 1999, 40, 2747.
44. (h) Kang, S.-K.; Lee, S.-H.; Lee, D. Synlett 2000, 1022.
45. (i) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A. Synlett 2000, 674.
46. For selected recent papers on the synthesis of N-aryl imidazoles via other transformations, see: (a) Lee, S.-H.; Yoshida, K.; Matsushita, H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Org. Chem. 2004, 69, 8829.
47. (b) Li, W.; Lam, Y. J. Comb. Chem. 2005, 7, 644.
48. (c) Gracias, V.; Gasiecki, A. F.; Djuric, S. W. Org. Lett. 2005, 7, 3183.
49. (d) Szczepankiewicz, B. G.; Rohde, J. J.; Kurukulasuriya, R. Org. Lett. 2005, 7, 1833.
50. (e) Siamaki, A. R.; Arndtsen, B. A. J. Am. Chem. Soc. 2006, 128, 6050.
51. For a paper on the solvent-free copper-catalyzed amination reactions of aryl halides with amines, see: Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 1994.
52. (a) Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Synlett 2005, 1897.
53. (b) Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Eur. J. Org. Chem. 2005, 4256.
54. (a) Li, J.-H.; Deng, C.-L.; Xie, Y.-X. Synthesis 2006, 969.
55. (b) Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379.
56. (a) Lindley, J. Tetrahedron 1984, 40, 1433.
57. (b) Cohen, T.; Wood, J.; Dietz, A. G., Jr. Tetrahedron Lett. 1974, 15, 3555.
58. (c) Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496.
59. (d) Aalten, H. L.; van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565.
60. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.