New efficient synthesis of 1,2,4-trisubstituted imidazoles and imidazo[1,2-c]quinazolines by a tandem aza-Wittig/electrocyclic ring-closure process

Tetrahedron

Volumn 68, Issue 4, 2012, Pages 965-971

  Nie, Yi Bo ^a   Duan, Zhuan ^a   Ding, Ming Wu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; IMIDAZOLE DERIVATIVE; ISOCYANATE; QUINAZOLINE DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; PRIORITY JOURNAL; RING CLOSING METATHESIS; ROOM TEMPERATURE; SYNTHESIS; WITTIG REACTION;

EID: 84855442426     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.005     Document Type: Article

References (50)

1. C.F. Claiborne, N.J. Liverton, and K.T. Nguyen Tetrahedron Lett. 39 1998 8939
2. Y. Özkay, Iikda, Z. ncesu, and G. Akalin Eur. J. Med. Chem. 45 2010 3320
3. B. Cui, B.L. Zheng, K. He, and Q.Y. Zheng J. Nat. Prod. 66 2003 1101
4. J.Z. Vlahakis, R.T. Kinobe, R.J. Bowers, J.F. Brien, K. Nakatsu, and W.A. Szarek J. Med. Chem. 49 2006 4437
5. A.K. Takle, M.J.B. Brown, S. Davies, D.K. Dean, G. Francis, A. Gaiba, A.W. Hird, F.D. King, P.J. Lovell, A. Naylor, A.D. Reith, J.G. Steadman, and D.M. Wilson Bioorg. Med. Chem. Lett. 16 2006 378
6. Schmierer, R.; Mildenberger, H.; Buerstell, H. German Patent 361464, 1987
7. Chem. Abstr. 108 1988 37838
8. Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. U.S. Patent 4820335, 1989
9. Chem. Abstr. 111 1989 19494w
10. S. Carmely, M. Ilan, and Y. Kashman Tetrahedron 45 1989 2193
11. K.A. Alvi, and P. Crews J. Nat. Prod. 54 1991 1509
12. K.A. Alvi, B.M. Peters, L.M. Hunter, and P. Crews Tetrahedron 49 1993 329
13. A.V. Gulevich, E.S. Balenkova, and V.G. Nenajdenko J. Org. Chem. 72 2007 7878
14. K. Sung, S.H. Wu, and P.I. Chen Tetrahedron 58 2002 5599
15. C. Zhang, E.J. Moran, T.F. Woiwode, K.M. Short, and A.M.M. Mjalli Tetrahedron Lett. 37 1996 751
16. S. Samai, G.C. Nandi, P. Singh, and M.S. Singh Tetrahedron 65 2009 10155
17. Y.M. Kim, S. Lee, S.H. Kim, K.H. Kim, and J.N. Kim Tetrahedron Lett. 51 2010 5922
18. J.M. Cobb, N. Grimster, N. Khan, J.Y.Q. Lai, H.J. Payne, L.J. Payne, T. Raynham, and J. Taylor Tetrahedron Lett. 43 2002 7557
19. S. Petit, C. Fruit, and L. Bischoff Org. Lett. 12 2010 4928
20. S. Zaman, K. Mitsuru, and A.D. Abell Org. Lett. 7 2005 609
21. S.P. Marsden, A.E. McGonagle, and B. McKeever-Abbas Org. Lett. 10 2008 2589
22. D. Lertpibulpanya, S.P. Marsden, I. Rodriguez-Garcia, and C.A. Kilner Angew. Chem., Int. Ed. 45 2006 5000
23. F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, and J.M. Santos Tetrahedron 63 2007 523
24. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, and R.-A. Orenes Org. Biomol. Chem. 8 2010 4690
25. N.O. Devarie-Baez, and M. Xian Org. Lett. 12 2010 752
26. P. Molina, P.M. Fresneda, and P. Alarcon Tetrahedron Lett. 29 1988 379
27. J. Barluenga, M. Ferrero, and F. Palacios J. Chem. Soc., Perkin Trans. 1 1990 2193
28. P. Molina, A. Pastor, and M.J. Vilaplana Tetrahedron 49 1993 7769
29. P. Molina, A. Tarraga, and M.J. Lidon J. Chem. Soc., Perkin Trans. 1 1990 1727
30. T. Saito, M. Nakane, M. Endo, H. Yamashita, Y. Oyamade, and S. Motoki Chem. Lett. 1986 135
31. C. Bonini, M. D'Auria, M. Funicello, and G. Romaniello Tetrahedron 58 2002 3507
32. A. Degl'Innocenti, M. Funicello, P. Scafato, P. Spagnolo, and P. Zanirato J. Chem. Soc., Perkin Trans. 1 1996 2561
33. C. Peinador, M.J. Moreira, and J.M. Quintela Tetrahedron 50 1994 6705
34. P. Molina, E. Aller, A. Lorenzo, P. López-Cremades, I. Rioja, A. Ubeda, M.C. Terencio, and M.J. Alcaraz J. Med. Chem. 44 2001 1011
35. P. Molina, A. Lorenzo, and E. Aller Tetrahedron 48 1992 4601
36. P.M.S. Bedi, V. Kumar, and M.P. Mahajan Bioorg. Med. Chem. Lett. 14 2004 5211
37. E. Rossi, D. Calabrese, and F. Farma Tetrahedron 47 1991 5819
38. F. Palacios, C. Alonso, and G. Rubiales Tetrahedron 51 1995 3683
39. Y. Zhong, L. Wang, and M.W. Ding Tetrahedron 67 2011 3714
40. P. He, Y.B. Nie, J. Wu, and M.W. Ding Org. Biomol. Chem. 9 2011 1429
41. P. He, J. Wu, Y.B. Nie, and M.W. Ding Eur. J. Org. Chem. 2010 1088
42. W.J. Li, S. Liu, P. He, and M.W. Ding Tetrahedron 66 2010 8151
43. N.Y. Huang, Y.B. Nie, and M.W. Ding Synlett 2009 611
44. W.J. Li, F.F. Zhao, and M.W. Ding Synlett 2011 265
45. P. He, J. Wu, Y.B. Nie, and M.W. Ding Tetrahedron 65 2009 8563
46. N.Y. Huang, M.G. Liu, and M.W. Ding J. Org. Chem. 74 2009 6874
47. G. L'abbé, and A. Hassner J. Org. Chem. 36 1971 258
48. A. Hassner, G. L'abbé, and M.J. Miller J. Am. Chem. Soc. 93 1971 981
49. L.C. Fardelone, J. Augusto, R. Rodrigues, and P.J.S. Moran J. Mol. Catal. B: Enzym. 29 2004 41
50. M.V. George, A. Mitra, and K.B. Sukumaran Angew. Chem., Int. Ed. Engl. 19 1980 973