Facile one-pot synthesis of N-alkylated benzimidazole and benzotriazole from carbonyl compounds

Journal of Heterocyclic Chemistry

Volumn 51, Issue 2, 2014, Pages 349-356

  Meng, Xu ^a   Li, Xiaolong ^a   Chen, Wenlin ^a   Zhang, Yuanqing ^a   Wang, Wen ^a   Chen, Jinying ^a   Song, Jinli ^a   Feng, Huijie ^b   Chen, Baohua ^a  

^a LANZHOU UNIVERSITY   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYL GROUP; BENZIMIDAZOLE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CARBONYL DERIVATIVE; COPPER; HETEROCYCLIC COMPOUND; HYDRAZIDE DERIVATIVE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROGEN BOND; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84897374184     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1616     Document Type: Article

References (53)

1. (a), Bai, Y.,;, Lu, J.,;, Shi, Z.,;, Yang, B., Synlett 2001, 4, 544
2. (b), Hasegawa, E.,;, Yoneoka, A.,;, Suzuki, K.,;, Kato, T.,;, Kitazume, T.,;, Yangi, K., Tetrahedron 1999, 55, 12957.
3. (a), Katritzky, A. R.,;, Rachwal, S., Chem Rev 2010, 110, 1564
4. (b), Katritzky, A. R.,;, Lan, X.,;, Yang, J. Z.,;, Denisko, O. V., Chem Rev 1998, 98, 409
5. (c), Bouwman, E.,;, Driessen, W. L.,;, Reedjik, J., Coord Chem Rev 1990, 104, 143
6. (d), Pujar M. A.,;, Bharamgoudar, T. D., Transition Met. Chem. 1988, 13, 423.
7. (a), Erhardt, P. W. J., Med Chem 1987, 30, 231
8. (b), Gravalt, G. L.,;, Baguley, B. C.,;, Wilson, W. R.,;, Denny, W. A. J., Med Chem 1994, 37, 4338
9. (c), Soderlind, K.-J.,;, Gorodetsky, B.,;, Singh, A. K.,;, Bachur, N.,;, Miller, G. G.,;, Loun, J. W., Anti-Cancer Drug Des. 1999, 14, 19
10. (d), Kim, J. B.,;, Gatto, B.,;, Yu, C.,;, Liu, A.,;, Liu, L. F.,;, Lavoie, E. J. J., Med Chem 1996, 39, 992.
11. For examples, see: (a), Al-Azmi, A.,;, George, P.,;, El-Dusouqui, O. M. E. J., Heterocycl. Chem. 2007, 44, 515
12. (b), Begtrup, M.,;, Larsen, P., Acta Chem Scand 1990, 44, 1050.
13. Fulton, J. R.,;, Aggarwal, V. K.,;, de Vicente, J., Eur J Org Chem 2005, 8, 1479.
14. (a), Barluenga, J.,;, Tomás-Gamasa, M.,;, Aznar, F.,;, Valdés, C., Nat Chem 2009, 1, 433
15. (b), Barluenga, J.,;, Tomás-Gamasa, M.,;, Aznar, F.,;, Valdés, C., Angew Chem Int Ed 2010, 49, 4993
16. (c), Barluenga, J.,;, Tomás-Gamasa, M.,;, Aznar, F.,;, Valdés, C., Eur J Org Chem 2011, 8, 1520
17. (d), Barluenga, J.,;, Tomás-Gamasa, M.,;, Aznar, F.,;, Valdés, C., Adv Synth Catal 2010, 352, 3235
18. (e), Barluenga, J.,;, Tomás-Gamasa, M.,;, Moriel, P.,;, Aznar, F.,;, Valdés, C., Chem Eur J 2008, 14, 4792
19. (f), Barluenga, J.,;, Moriel, P.,;, Valdés, C.,;, Aznar, F., Angew Chem Int Ed 2007, 46, 5587
20. (g), Barluenga, J.,;, Florentino, L.,;, Aznar, F.,;, Valdés, C., Org Lett 2011, 13, 510
21. (h), Barluenga, J.,;, Escribano, M.,;, Aznar, F.,;, Valdés, C., Angew Chem Int Ed 2010, 49, 6856
22. (i), Barluenga, J.,;, Tomás-Gamasa, M.,;, Aznar, F.,;, Valdés, C., Chem Eur J 2010, 16, 12801
23. (j), Barluenga, J.,;, Escribano, M.,;, Moriel, P.,;, Aznar, F.,;, Valdés, C., Chem Eur J 2009, 15, 13291
24. (k), Barluenga, J.,;, Valdés, C., Angew Chem Int Ed 2011, 50, 7486.
25. (a), Zhao, X.,;, Wu, G.,;, Zhang, Y.,;, Wang, J. J., Am Chem Soc 2011, 133, 3296
26. (b), Xiao, Q.,;, Ma, J.,;, Yang, Y.,;, Zhang, Y.,;, Wang, J., Org Lett 2009, 11, 4732
27. (c), Zhao, X.,;, Jing, J.,;, Lu, K.,;, Zhang, Y.,;, Wang, J., Chem Commun 2010, 46, 1724
28. (d), Xiao, Q.,;, Xia, Y.,;, Li, H.,;, Zhang, Y.,;, Wang, J., Angew Chem Int Ed 2011, 50, 1114
29. (e), Zhou, L.,;, Shi, Y.,;, Xiao, Q.,;, Liu, Y.,;, Ye, F.,;, Zhang, Y.,;, Wang, J., Org Lett 2011, 13, 968
30. (f), Ye, F.,;, Shi, Y.,;, Zhou, L.,;, Xiao, Q.,;, Zhang, Y.,;, Wang, J., Org Lett 2011, 13, 5020.
31. (a), Tréguier, B.,;, Hamze, A.,;, Provot, O.,;, Brion, J.-D.,;, Alami, M., Tetrahedron Lett 2009, 50, 6549
32. (b), Rasolofonjatovo, E.,;, Tréguier, B.,;, Provot, O.,;, Hamze, A.,;, Morvan, E.,;, Brion, J.-D.,;, Alami, M., Tetrahedron Lett 2011, 52, 1036
33. (c), Brachet, E.,;, Hamze, A.,;, Peyrat, J.-F.,;, Brion, J.,;, Alami, M., Org Lett 2010, 12, 4042.
34. (a), Zhang, J.,;, Chan, P. W. H.,;, Che, C.-M., Tetrahedron Lett 2003, 44, 8733
35. (b), Cheung, W.-H.,;, Zheng, S.-L.,;, Yu, W.-Y.,;, Zhou, G.-C.,;, Che, C.-M., Org Lett 2003, 5, 2535
36. (c), Feng, X.-W.,;, Wang, J.,;, Zhang, J.,;, Yang, J.,;, Wang, N.,;, Yu, X.-Q., Org Lett 2010, 12, 4408
37. (d), Ding, Q.,;, Cao, B.,;, Yuan, J.,;, Liu, X.,;, Peng, Y., Org Biomol Chem 2011, 9, 748
38. (e), Chen, Z.,;, Yu, X.,;, Wu, J., Chem Commun 2010, 46, 6356
39. (f), E. Cuevas-Yañez, E. Serrano, J. M. Huerta, G. Muchowskib, J. M. Cruz-Almanza, R Tetrahedron 2004, 60, 9391
40. (g), Shao, Z.,;, Zhang, H., Chem Soc Rev 2012, 41, 560.
41. Literatures on N-H functionalization by carbene insertion from diazo compounds: (a), Bagley, M. C.,;, Buck, R. T.,;, Hind, S. L.,;, Moody, C. J., J Chem Soc, Perkin Trans 1 1998, 3, 591
42. (b), Moody, C. J.,;, Bagley, M. C., J Chem Soc, Perkin Trans 1 1998, 3, 601
43. (c), Bagley, M. C.,;, Bashford, K. E.,;, Hesketh, C. L.,;, Moody, C. J., J Am Chem Soc 2000, 122, 3301
44. (d), Wang, J.,;, Hou, Y.,;, Wu, P., J Chem Soc, Perkin Trans 1 1999, 16, 2277.
45. Review on transition-metal-catalyzed cross-coupling reaction: (a), Monnier, F.,;, Taillefer, M., Angew Chem Int Ed 2009, 48, 6954
46. (b), Ley, S. V.,;, Thomas, A. W., Angew Chem Int Ed 2003, 42, 5400.
47. 3 C-H bond adjacent to heteroatoms: (a), Li, Z.,;, Yu, R.,;, Li, H., Angew Chem Int Ed 2008, 47, 7497
48. (b), Niu, M.,;, Yin, Z.,;, Fu, H.,;, Jiang, Y.,;, Zhao, Y. J., Org Chem 2008, 73, 3961
49. (c), Liu, X.,;, Zhang, Y.,;, Wang, L.,;, Fu, H.,;, Jiang, Y.,;, Zhao, Y. J., Org Chem 2008, 73, 6207
50. (d), Li, Z.,;, Li, C. J., Am Chem Soc 2005, 127, 3672.
51. Davies, H. M. L.,;, Manning, J. R., Nature 2008, 451, 471.
52. Zhang, Z.,;, Wang, J., Tetrahedron 2008, 64, 6577.
53. Katritzky, A. R.,;, Puschmann, I. B.,;, Stevens, C. V.,;, Wells, A. P., J Chem Soc, Perkin Trans 2 1995, 8, 1645.