Remarkable Rate Acceleration of Imidazole-Promoted Baylis-Hillman Reaction Involving Cyclic Enones in Basic Water Solution

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 555-558

  Luo, Sanzhong ^a   Wang, Peng George ^c   Cheng, Jin Pei ^a,b  

^a INSTITUTE OF CHEMISTRY   (China)

^b NANKAI UNIVERSITY   (China)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACCELERATION; ALKALINITY; CATALYSTS;

REACTION MEDIUM;

REACTION KINETICS;

IMIDAZOLE; WATER;

ACCELERATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; REACTION TIME;

EID: 0346502285     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035345p     Document Type: Article

References (46)

1. (a) Ciganek, E. Org. React. 1997, 51, 201.
2. (b) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
3. (c) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
4. Ultrasound: (a) Roos, G. H. P.; Rampersadh, P. Synth. Commun. 1993, 23, 1261.
5. (b) Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609.
6. (c) Coelho, F.; Almeida, W. P.; Veronese, D.; Mateus, C. R.; Lopes, E. C. S.; Rossi, R. C.; Silveira, G. P. C.; Pavam, C. H. Tetrahedron 2002, 58, 7437.
7. Microwave: (c) Kundu, M. K.; Mukherjee, S. B.; Balu, N.; Padmakumar, R.; Bhat, S. V. Synlett 1994, 444.
8. (d) Cablewski, T.; Faux, A. F.; Strauss, C. R. J. Org. Chem. 1994, 59, 3408.
9. High pressure: (e) Hayashi, Y.; Okada, K.; Ashimine, I.; Shoji, M. Tetrahedron Lett. 2002, 43, 8683.
10. (f) Schuurman, R. J. W.; vander-Linden A.; Grimbergen, R. P. F.; Nolte, R. J. M.; Scheeren, H. W. Tetrahedron 1996, 54, 8307.
11. (g) Hill, J. S.; Isaacs, M. S. Tetrahedron Lett. 1986, 27, 5007.
12. Low temperature: (h) Rafel, S.; Leahy, J. W. J. Org. Chem. 1997, 62, 1521.
13. Lewis acid: (i) Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 1539.
14. (j) Aggarval, V. K.; Mereu, A.; Farver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
15. (k) Kataoka, T.; Iwama, T.; Tsujiyama, S. Chem. Commun. 1997, 197.
16. (l) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2, 2397.
17. For other examples, see: (m) Aggarwal, V. K.; Mereu, A. Chem. Commun. 1999, 2311.
18. (n) Lee, W.-D.; Yang, K.-S.; Chen, K. Chem. Coummn. 2001, 1612.
19. (o) Anthony, P. M. R.; Clifford, A. A.; Rayner, C. M. Chem. Commun. 2002, 968.
20. (p) Rosa, J. N.; Afonso, C. A. M.; Santos, A. G. Tetrahedron Lett. 2001, 57, 4189.
21. (a) Byun, H. S.; Reddy, K. C.; Bittman, R. Tetrahedron Lett. 1994, 35, 1371.
22. (b) Auge, J.; Lubin, N.; Lubineau, A. Tetrahedron Lett. 1994, 35, 7947.
23. (c) Rezgui, F.; El Gaied, M. M. Tetrahedron lett. 1998, 39, 5965.
24. (a) Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413.
25. (b) Yu, C.; Hu, L. J. Org. Chem. 2002, 67, 219.
26. (c) Cai, J.; Zhou, Z.; Zhao, G.; Tang, C. Org. Lett. 2002, 4, 4723.
27. (a) Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510.
28. (b) Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692.
29. For examples, see: (a) Li, G. G.; Wei, H. X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1.
30. (b) Sugahara, T.; Ogasawara, K. Synlett 1999, 419.
31. (c) Kataoka, T.; Iwama, T.; Tsujiyama, S.; Iwamura, T.; Watanabe, S. Tetrahedron 1998, 54, 11813.
32. (d) Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165.
33. (e) Pei, W.; Wei, H.-X.; Li, G. G. Chem. Commun. 2002, 2412.
34. (e) Basavaiah, D.; Sreenivasulu, B.; Rao, A. J. J. Org. Chem. 2003, 68, 5983.
35. (f) Patra, A.; Batra, S.; Joshi, B. S.; Roy, R.; Kundu, B.; Bhaduri, A. P. J. Org. Chem. 2002, 67, 5783.
36. (g) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666.
37. (a) Luo, S. Z.; Zhang, B.; He, J.; Janczuk, A.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2002, 43, 7369.
38. (b) Catri, R.; El Gaied, M. M. Tetraheron Lett. 2002, 43, 7835.
39. For similar proton transfer of imidazole in biological systems, see: (a) Silverman, D. N.; Lindskog, S. Acc. Chem. Res. 1988, 21, 30.
40. (b) Lesburg, C. A.; Christianson, D. W. J. Am. Chem. Soc. 1995, 117, 6838.
41. Schneider, F. Angew. Chem., Int. Ed. Engl. 1978, 17, 583 and references therein.
42. (a) Alei, M. Jr.; Morgan, L. O.; Wageman, W. E. Inorg. Chem. 1978, 17, 2288.
43. (b) Alei, M. Jr.; Morgan, L. O.; Wageman, W. E.; Whaley, T. W. J. Am. Chem. Soc. 1980, 102, 2881.
44. 3 solution after 1.5 h. While in the presence of imidazole the Baylis-Hillman reaction predominated with trace aldol products detected.
45. a8.36). For salt effects in aqueous Baylis-Hillman reaction, see: Kumar, A.; Pawar, S. S. Tetrahedron 2003, 59, 5019.
46. a values of imidazoles see: Schofield, K.; Grimmett, M. R.; Keene, B. R. T. Heteroaromatic nitrogen compounds: the azoles; Cambridge University Press: Cambridge, 1976; p 281.