Synthesis of 1,2,4,5-tetrasubstituted imidazoles by a sequential aza-Wittig/Michael/isomerization reaction

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 696-700

  Nie, Yi Bo ^a   Wang, Long ^a   Ding, Ming Wu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AIR OXIDATION; ALKOXIDES; ARYL ISOCYANATES; AZA-WITTIG REACTION; CARBODIIMIDES; CATALYTIC AMOUNTS; GOOD YIELD; IMINOPHOSPHORANES; SECONDARY AMINES;

CATALYTIC OXIDATION; PHENOLS; POTASSIUM; SODIUM;

SYNTHESIS (CHEMICAL);

ETHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (DIBUTYLAMINO) 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (DIETHYLAMINO) 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (PIPERIDIN 1 YL) 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (PYRROLIDIN 1 YL) 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 MORPHOLINO 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 1 (4 FLUOROPHENYL) 2 MORPHOLINO 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 2 MORPHOLINO 1 (3 TOLYL) 1H IMIDAZOL 5 YL]ACETATE; ETHYL 2 [4 BENZYL 2 MORPHOLINO 1 (4 TOLYL) 1H IMIDAZOL 5 YL]ACETATE; IMIDAZOLE DERIVATIVE; METHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (PIPERIDIN 1 YL) 1H IMIDAZOL 5 YL]ACETATE; METHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 (PYRROLIDIN 1 YL) 1H IMIDAZOL 5 YL]ACETATE; METHYL 2 [4 BENZYL 1 (4 CHLOROPHENYL) 2 MORPHOLINO 1H IMIDAZOL 5 YL]ACETATE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; MICHAEL ADDITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SEQUENTIAL AZA WITTIG REACTION; SUBSTITUTION REACTION;

CARBODIIMIDES; CATALYSIS; IMIDAZOLES; ISOMERISM; MOLECULAR STRUCTURE;

EID: 84862908836     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201846w     Document Type: Article

References (47)

1. Rahman, M. N.; Vlahakis, J. Z.; Szarek, W. A.; Nakatsu, K.; Jia, Z. J. Med. Chem. 2008, 51, 5943-5952
2. Bowles, D. M.; Bolton, G. L.; Boyles, D. C.; Curran, T. T.; Hutchings, R. H.; Larsen, S. D.; Miller, J. M.; Park, W. K. C.; Ritsema, K. G.; Schineman, D. C. Org. Process Res. Dev. 2008, 12, 1183-1187
3. Sugishima, M.; Higashimoto, Y.; Oishi, T.; Takahashi, H.; Sakamoto, H.; Noguchi, M.; Fukuyama, K. Biochemistry 2007, 46, 1860-1867
4. Sit, S. Y.; Conway, C.; Bertekap, R.; Xie, K.; Bourin, C.; Burris, K.; Deng, H. Bioorg. Med. Chem. Lett. 2007, 17, 3287-3291
5. Madsen, C.; Jensen, A. A.; Liljefors, T.; Kristiansen, U.; Nielsen, B.; Hansen, C. P.; Larsen, M.; Ebert, B.; Bang-Andersen, B.; Krogsgaard-Larsen, P.; Frølund, B. J. Med. Chem. 2007, 50, 4147-4161
6. Gleave, R. J.; Walter, D. S.; Beswick, P. J.; Fonfria, E.; Michel, A. D.; Roman, S. A.; Tang, S.-P. Bioorg. Med. Chem. Lett. 2010, 20, 4951-4954
7. Menge, W. M. P. B.; Timmerman, H. Pharmacochem. Libr. 1998, 30, 145
8. Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754
9. Sung, K.; Wu, S. H.; Chen, P. I. Tetrahedron 2002, 58, 5599-5602
10. Gulevich, A. V.; Balenkova, E. S.; Nenajdenko, V. G. J. Org. Chem. 2007, 72, 7878-7885
11. Zificsak, C. A.; Hlasta, D. J. Tetrahedron Lett. 2005, 46, 4789-4792
12. Torregrosa, R.; Pastor, I. M.; Yus, M. Tetrahedron 2005, 61, 11148-11155
13. Pridgen, L. N.; Mokhallalti, M. K.; McGuire, M. A. Tetrahedron Lett. 1997, 38, 1275-1278
14. Xi, N.; Xu, S.; Cheng, Y.; Tasker, A. S.; Hungate, R. W.; Reider, P. J. Tetrahedron Lett. 2005, 46, 7315-7319
15. Chen, J. J.; Zhang, Y.; Hammond, S.; Dewdney, N.; Ho, T.; Lin, X.; Browner, M. F.; Castelhano, A. L. Bioorg. Med. Chem. Lett. 1996, 6, 1601-1606
16. Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516-1524
17. Sisko, J. J. Org. Chem. 1998, 63, 1516-1524
18. Marsden, S. P.; McGonagle, A. E.; McKeever-Abbas, B. Org. Lett. 2008, 10, 2589-2591
19. Lertpibulpanya, D.; Marsden, S. P.; Rodriguez-Garcia, I.; Kilner, C. A. Angew. Chem., Int. Ed. 2006, 45, 5000-5002
20. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; Santos, J. M. Tetrahedron 2007, 63, 523-575
21. Alajarin, M.; Bonillo, B.; Ortin, M.-M.; Sanchez-Andrada, P.; Vidal, A.; Orenes, R.-A. Org. Biomol. Chem. 2010, 8, 4690-4700
22. Devarie-Baez, N. O.; Xian, M. Org. Lett. 2010, 12, 752-754
23. Molina, P.; Fresneda, P. M.; Sanz, M. A. J. Org. Chem. 1999, 64, 2540-2544
24. Palacios, F.; Legido, M.; Pérez de Heredia, I.; Rubiales, G.; Ezpeleta, J. M. Heterocycles 2001, 55, 1641-1651
25. Molina, P.; Pastor, A.; Vilaplana, M. J. Tetrahedron Lett. 1996, 37, 7829-7832
26. Molina, P.; Tárraga, A.; Curiel, D.; Ramírez de Arellano, C. Tetrahedron 1999, 55, 1417-1426
27. Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405-1407
28. Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc., Perkin Trans. 1 1996, 247-254
29. Blanco, G.; Quintela, J. M.; Peinador, C. Tetrahedron 2007, 63, 2034-2041
30. Blanco, G.; Fernández-Mato, A.; Quintela, J. M.; Peinador, C. Tetrahedron 2008, 64, 11136-11143
31. Saito, T.; Tsuda, K.; Saito, Y. Tetrahedron Lett. 1996, 37, 209-212
32. Wang, F.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 8651-8654
33. Zhong, Y.; Wang, L.; Ding, M. W. Tetrahedron 2011, 67, 3714-3723
34. He, P.; Nie, Y. B.; Wu, J.; Ding, M. W. Org. Biomol. Chem. 2011, 9, 1429-1436
35. He, P.; Wu, J.; Nie, Y. B.; Ding, M. W. Eur. J. Org. Chem. 2010, 1088-1095
36. Li, W. J.; Liu, S.; He, P.; Ding, M. W. Tetrahedron 2010, 66, 8151-8159
37. Huang, N. Y.; Nie, Y. B.; Ding, M. W. Synlett 2009, 611-614
38. Li, W. J.; Zhao, F. F.; Ding, M. W. Synlett 2011, 265-267
39. He, P.; Wu, J.; Nie, Y. B.; Ding, M. W. Tetrahedron 2009, 65, 8563-8570
40. Huang, N. Y.; Liu, M. G.; Ding, M. W. J. Org. Chem. 2009, 74, 6874-6877
41. Huang, N. Y.; Liang, Y. J.; Ding, M. W.; Fu, L. W.; He, H. W. Bioorg. Med. Chem. Lett. 2009, 19, 831-833
42. Liu, M. G.; Hu, Y. G.; Ding, M. W. Tetrahedron 2008, 64, 9052-9059
43. Li, H. X.; Xie, C.; Ding, M. W.; Liu, Z. M.; Yang, G. F. Synlett 2007, 2280-2282
44. Ding, M. W.; Xu, S. Z.; Zhao, J. F. J. Org. Chem. 2004, 69, 8366-8371
45. L'abbé, G.; Hassner, A. J. Org. Chem. 1971, 36, 258-260
46. Hassner, A.; L'abbé, G.; Miller, M. J. J. Am. Chem. Soc. 1971, 93, 981-985
47. Fardelone, L. C.; Augusto, J.; Rodrigues, R.; Moran, P. J. S. J. Mol. Catal. B: Enzym. 2004, 29, 41-45