1-Methylimidazole 3-N-oxide as a new promoter for the Morita-Baylis-Hillman reaction

Tetrahedron Letters

Volumn 46, Issue 11, 2005, Pages 1859-1861

  Lin, Yu Sheng ^a   Liu, Chih Wei ^a   Tsai, Thomas Y R ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

Morita Baylis Hillman reaction; N oxide

Indexed keywords

1 METHYLIMIDAZOLE 3 N OXIDE; ALDEHYDE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; LEWIS BASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; MORITA BAYLIS HILLMAN REACTION; REACTION ANALYSIS;

EID: 13944257407     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.099     Document Type: Article

References (42)

1. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jpn. 41 1968 2815
2. C. Yu, and L. Hu J. Org. Chem. 67 2002 219
3. A. Patra, A.K. Roy, B.S. Joshi, R. Roy, S. Batra, and A.P. Bhaduri Tetrahedron 59 2003 663
4. M. Shi, and G.L. Zhao Tetrahedron 60 2004 2083
5. D.J. Maher, and S.J. Connon Tetrahedron Lett. 45 2004 1301
6. S. Chandrasekhar, C. Narsihmulu, B. Saritha, and S.S. Sultana Tetrahedron Lett. 45 2004 5865
7. F. Rezgui, and M.M. E1 Gaïed Tetrahedron Lett. 39 1998 5965
8. Y. Sohtome, A. Tanatani, Y. Hashimoto, and K. Nagasawa Tetrahedron Lett. 45 2004 5589
9. V.K. Aggarwal, and A. Mereu Chem. Commun. 1999 2311
10. R. Ballini, L. Barboni, G. Bosica, D. Fiorini, E. Mignini, and A. Palmieri Tetrahedron 60 2004 4995
11. T. Hayase, T. Shibata, K. Soai, and Y. Wakasuki Chem. Commun. 1998 2533
12. T. Kataoka, T. Iwama, and S. Tsujiyama Chem. Commun. 1998 197
13. C. Yu, B. Liu, and L. Hu J. Org. Chem. 66 2001 5413
14. B. Alcaid, P. Almendros, and C. Aragoncillo J. Org. Chem. 66 2001 1612
15. S. Luo, B. Zhang, J. He, A. Janczuk, P.G. Wang, and J. Cheng Tetrahedron Lett. 43 2002 7369
16. R. Gatri, and M.M. E1 Gaïed Tetrahedron Lett. 43 2002 7835
17. T. Kataoka, H. Kinoshita, S. Kinoshita, T. Iwamura, and S. Watanabe Angew. Chem., Int. Ed. 39 2000 2358
18. M. Shi, J.-K. Jiang, and Y.S. Feng Org. Lett. 2 2000 2397
19. M. Shi, and J.K. Jiang Tetrahedron 56 2000 4793
20. G. Li, H.X. Wei, J.J. Gao, and T.D. Caputo Tetrahedron Lett. 41 2000 1
21. M. Shi, and Y.S. Feng J. Org. Chem. 66 2001 406
22. M. Shi, J.-K. Jiang, and S.-C. Cui Tetrahedron 57 2001 7343
23. A. Patra, S. Batra, B.S. Joshi, R. Roy, B. Kundu, and A.P. Bhaduri J. Org. Chem. 67 2002 5783
24. D. Basavaiah, B. Sreenivasulu, and A.J. Rao J. Org. Chem. 68 2003 5983
25. W. Pei, H. Wei, and G. Li Chem. Commun. 2002 1856
26. W. Pei, H. Wei, and G. Li Chem. Commun. 2002 2412
27. H. Kinoshita, S. Kinoshita, Y. Munechika, T. Iwamura, S. Watanabe, and T. Kataoka Eur. J. Org. Chem. 2003 4852
28. H. Kinoshita, T. Osamura, S. Kinoshita, T. Iwamura, S. Watanabe, T. Kataoka, G. Tanabe, and O. Muraoka J. Org. Chem. 68 2003 7532
29. V.K. Aggarwal, D.K. Dean, A. Mereu, and R. Williams J. Org. Chem. 67 2002 510
30. P.R. Krishna, A. Manjuvani, V. Kannan, and G.V.M. Sharma Tetrahedron Lett. 45 2004 1183
31. S. Luo, X. Mi, P.G. Wang, and J.P. Cheng Tetrahedron Lett. 45 2004 5171
32. T. Oishi, H. Oguri, and M. Hirama Tetrahedron: Asymmetry 6 1995 1241
33. Y. Hayashi, K. Okado, I. Ashimine, and M. Shoji Tetrahedron Lett. 43 2002 8683
34. M.K. Kundu, S.B. Mukherjee, N. Balu, R. Padmakumar, and S.V. Bhat Synlett 1994 444
35. W.P. Almeida, and F. Coelho Tetrahedron Lett. 39 1998 8609
36. F. Coelho, W.P. Almeida, D. Veronese, C.R. Mateus, E.C. Silva Lopes, R.C. Rossi, G.P.C. Silveira, and C.H. Pavam Tetrahedron 58 2002 7437
37. S. Luo, P.G. Wang, and J. Cheng J. Org. Chem. 69 2004 555
38. A. Kumar, and S.S. Pawar Tetrahedron 59 2003 5019
39. 4 and concentrated. A light yellow oil, 1-methylimidazole 3-N-oxide, was obtained (8.93 g, 95%)
40. In order to reduce the reaction time, we tried to increase the catalyst amount of compound 1 (0.5-5 equiv). The use of a small amount of 3-N-oxide (0.5-1 equiv) resulted in lower conversion yield and longer reaction time. We found 2 equiv of compound 1 is the best condition for the Morita-Baylis-Hillman reaction
41. For example, 4-methoxybenzaldehyde (136 mg, 1 mmol), MVK (140 mg, 2 mmol) and 1-methylimidazole 3-N-oxide (196 mg, 2 mmol) were added a 10 mL flask. The reaction mixture was exposed to microwave irradiation (600 W) for 30 min
42. J.S. Hill, and N.S. Issacs J. Phys. Org. Phys. 1990 285