Practical multi-component synthesis of di-or tri-aryl (heteraryl) substituted 2-(pyridin-2-yl)imidazoles from simple building blocks

Journal of Combinatorial Chemistry

Volumn 12, Issue 6, 2010, Pages 829-835

  Wu, Xiao Jin ^a   Jiang, Ran ^a   Xu, Xiao Ping ^a   Su, Xiao Ming ^a   Lu, Wei Hong ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; IMIDAZOLES; MOLECULAR STRUCTURE; PYRIDINES;

EID: 78149340070     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc100079b     Document Type: Article

References (52)

1. Manley, P. J., Balitza, A. E., Bilodeau, M. T., Coll, K. E., Hartman, G. D., McFall, R. C., Rickert, K. W., Rodman, L. D., and Thomas, K. A. Bioorg. Med. Chem. Lett. 2003, 13, 1673-1677
2. Ring, D. B., Johnson, K. W., Henriksen, E. J., Nuss, J. M., Goff, D., Kinnick, T. R., Ma, S. T., Reeder, J. W., Samuels, I., Slabiak, T., Wagman, A. S., Hammond, M.-E. W., and Harrison, S. D. Diabetes 2003, 52, 588-595
3. Caron, S., Do, N. M., McDermott, R. E., and Bahmanyar, S. Org. Process Res. Dev. 2006, 10, 257-261
4. Murray, M. and Wilkinson, C. F. Chem. Biol. Interact. 1984, 50, 267-275
5. Vaher, B., Bonnaud, B., Funes, F., Jubault, N., Koek, W., Assie, M.-B., and Cosi, C. J. Med. Chem. 1998, 41, 5070-5083
6. Mano, T., Stevens, R. W., Ando, K., Okumura, Y., Sakakibara, M., Okumura, T., Tamura, T., and Miyamoto, K. Bioorg. Med. Chem. 2003, 11, 3879-3887
7. Akiharu, S., Hiroyuki, K., and Tadashi, N. Chem. Lett. 1999, 49-51
8. Wang, R., Xiao, J. C., Twamley, B., and Shreeve, J. M. Org. Biomol. Chem. 2007, 5, 671-678
9. Dupont, J., de Souza, R. F., and Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692
10. McManus, J. M. and Herbst, R. M. J. Org. Chem. 1959, 24, 1042-1044
11. Irving, H. and Weber, O. J. Chem. Soc. 1959, 2296-2298
12. Voss, M. E., Beer, C. M., Mitchell, S. A., Blomgren, P. A., and Zhichkin, P. E. Tetrahedron. 2008, 64, 645-651
13. Torelli, S., Delahaye, S., Hauser, A., Bernardinelli, G., and Piguet, C. Chem.-Eur. J. 2004, 10 (4) 3503-3516
14. Yang, D., Fokas, D., Li, J., Yu, L., and Baldino, C. M. Synthesis. 2005, 1, 47-56
15. Chattopadhyay, S. K., Mitra, K., Biswas, S., Lucas, C. R., and Adhikary, B. J. Chem. Res., Synop. 2003, 9, 562-563
16. Dubey, P. K., Kumar, C. R., and Reddy, V. P. Indian J. Chem., Sect B. 2003, 42 (9) 2115-2118
17. Romanenko, I. V., Sheinkman, A. K., Baranov, S. N., Poltavets, V. N., and Klyuev, N. A. Chem. Heterocycl. Compd. 1980, 16 (12) 1261-1267
18. Sharghi, H., Asemani, O., and Tabaei, S. M. H. J. Heterocycl. Chem. 2008, 45 (5) 1293-1298
19. Salehi, P., Dabiri, M., Zolfigol, M. A., Otokesh, S., and Baghbanzadeh, M. Tetrahedron Lett. 2006, 47 (15) 2557-2560
20. Matsushita, H., Lee, S. H., Joung, M., Clapham, B., and Janda, K. D. Tetrahedron Lett. 2004, 45 (2) 313-316
21. Jiang, B., Wang, X., Shi, F., Tu, S. J., Ai, T., Ballew, A., and Li, G. J. Org. Chem. 2009, 24, 9486-9489
22. Seko, N., Yoshino, K., Yokota, K., and Tsukamoto, G. Chem. Pharm. Bull. 1991, 39, 651-657
23. Kori, S. and Narisawa, S. Asahi Garasu Kenkyu Hokoku 1962, 12, 55-70
24. van Leusen, D. and van Leusen, A. M. Org. React. 2001, 57, 417-666
25. Radziszewski, B. Chem. Ber. 1882, 15, 1493-1496
26. App, J F. R. and Robinson, H. H. Chem. Ber. 1882, 15, 1268-1270
27. Valentina, Z., Giuseppe, C., Marco, F., Chiara, G., and Mirko, R. J. Org. Chem. 2007, 72, 4551-4553
28. Usyatinsky, A. Y. and Khemelnitsky, Y. L. Tetrahedron Lett. 2000, 41, 5031-5034
29. Wolkenberg, S. E., Wisnoski, D. D., Leister, W. H., Wang, Y., Zhao, Z., and Lindsley, C. W. Org. Lett. 2004, 6, 1453-1456
30. Sparks, R. B. and Combs, A. P. Org. Lett. 2004, 6, 2473-2478
31. Oskooie, H. A., Alimohamma di, Z., and Heravi, M. M. Heteroatom Chem. 2006, 17, 699-702
32. Siddiqui, S. A., Narkhede, U. C., Palimkar, S. S., Daniel, T., Lahoti, R. J., and Srinivasan, K. V. Tetrahedron 2005, 61, 3539-3546
33. Wang, J., Mason, R., Derveer, D. V., Feng, K., and Bu, X. R. J. Org. Chem. 2003, 68, 5415-5418
34. Sarshar, S., Siev, D., and Mjalli, M. M. Tetrahedron Lett. 1996, 37, 835-838
35. Domling, A. Chem. Rev. 2006, 106, 17-89
36. Domling, A. and Ugi, I. Angew, Chem, Int, Ed. 2000, 39, 3168-3210
37. Khalili, B., Tondro, T., and Hashemi, M. M. Tetrahedron. 2009, 65, 6882-6887
38. Zhu, S. L., Ji, S. J., Su, X. M., and Liu, Y. Tetrahedron Lett. 2008, 49, 1777-1781
39. Zhu, S. L., Ji, S. J., and Liu, Y. Tetrahedron Lett. 2008, 49, 2578-2582
40. Zhu, S. L., Ji, S. J., and Zhang, Y. Tetrahedron. 2007, 63, 9365-9372
41. Sun, C., Ji, S. J., and Liu, Y. Tetrahedron Lett. 2007, 48, 8987-8989
42. Zhao, K., Xu, X. P., Zhu, S. L., Shi, D. Q., Zhang, Y., and Ji, S. J. Synthesis 2009, 2697-2708
43. Wu, X. J., Xu, X. P., Su, X. M., and Ji, S. J. Eur. J. Org. Chem. 2009, 29, 4963-4970
44. -3, R [ I > 2σ(I)] = 0.0865, wR [ I > 2σ(I)] = 0. 2024.
45. Balalaie, S. and Arabanian, A. Green Chem. 2000, 2, 274-276
46. Karimi, A. R., Alimohammadi, Z., Azizian, J., Mohammadi, A. A., and Mohammadizadeh, M. R. Catal. Commun. 2006, 7, 728-732
47. Sadeghi, B., Mirjalili, B. B. F., and Hashemi, M. M. Tetrahedron Lett. 2008, 49, 2575-2577
48. -3, R [ I > 2σ(I)] = 0.0643, wR [ I > 2σ(I)] = 0.1606.
49. -3, R [ I > 2σ(I)] = 0.0472, wR [ I > 2σ(I)] = 0.1106.
50. Ohta, S. and Okamoto, M. Synthesis 1982, 756-758
51. Klappa, J. J., Rich, A. E., and McNeill, K. Org. Lett. 2002, 4, 435-437
52. -3, R [ I > 2σ(I)] = 0.0599, wR [ I > 2σ(I)] = 0.1480.