Facile synthesis of 2H-indazole derivatives starting from the Baylis-Hillman adducts of 2-cyclohexen-1-one

Tetrahedron Letters

Volumn 46, Issue 32, 2005, Pages 5387-5391

  Ka, Young Lee ^a   Gowrisankar, Saravanan ^a   Jae, Nyoung Kim ^a  

^a Chonnam National University   (South Korea)

Author keywords

2H Indazoles; Baylis Hillman adducts; Carbazoles; DDQ; Pyrazoles

Indexed keywords

2 CYCLOHEXENONE; 2,3 DICHLORO 5,6 DICYANO 1,4 BENZOQUINONE; INDAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG SYNTHESIS; OXIDATION;

EID: 22144459449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.149     Document Type: Article

References (36)

1. For the biological activities of indazole derivatives, see, J.-C. Lien, F.-Y. Lee, L.-J. Huang, S.-L. Pan, J.-H. Guh, C.-M. Teng, and S.-C. Kuo J. Med. Chem. 45 2002 4947
2. P.G. Baraldi, G. Balboni, M.G. Pavani, G. Spalluto, M.A. Tabrizi, E. De Clercq, J. Balzarini, T. Bando, H. Sugiyama, and R. Romagnoli J. Med. Chem. 44 2001 2536
3. D.L. Selwood, D.G. Brummell, J. Budworth, G.E. Burtin, R.O. Campbell, S.S. Chana, I.G. Charles, P.A. Fernandez, R.C. Glen, M.C. Goggin, A.J. Hobbs, M.R. Kling, Q. Liu, D.J. Madge, S. Meillerais, K.L. Powell, K. Reynolds, G.D. Spacey, J.N. Stables, M.A. Tatlock, K.A. Wheeler, G. Wishart, and C.-K. Woo J. Med. Chem. 44 2001 78
4. F.-Y. Lee, J.-C. Lien, L.-J. Huang, T.-M. Huang, S.-C. Tsai, C.-M. Teng, C.-C. Wu, F.-C. Cheng, and S.-C. Kuo J. Med. Chem. 44 2001 3746
5. H.-C. Zhang, C.K. Derian, P. Andrade-Gordon, W.J. Hoekstra, D.F. McComsey, K.B. White, B.L. Poulter, M.F. Addo, W.-M. Cheung, B.P. Damiano, D. Oksenberg, E.E. Reynolds, A. Pandey, R.M. Scarborough, and B.E. Maryanoff J. Med. Chem. 44 2001 1021
6. H.-J. Boehm, M. Boehringer, D. Bur, H. Gmuender, W. Huber, W. Klaus, D. Kostrewa, H. Kuehne, T. Luebbers, N. Meunier-Keller, and F. Mueller J. Med. Chem. 43 2000 2664
7. D.G. Batt, J.J. Petraitis, G.C. Houghton, D.P. Modi, G.A. Cain, M.H. Corjay, S.A. Mousa, P.J. Bouchard, M.S. Forsythe, P.P. Harlow, F.A. Barbera, S.M. Spitz, R.R. Wexler, and P.K. Jadhav J. Med. Chem. 43 2000 41
8. X. Li, S. Chu, V.A. Feher, M. Khalili, Z. Nie, S. Margosiak, V. Nikulin, J. Levin, K.G. Sprankle, M.E. Fedder, R. Almassy, K. Appelt, and K.M. Yager J. Med. Chem. 46 2003 5663
9. C. Giragossian, E.E. Sugg, J.R. Szewczyk, and D.F. Mierke J. Med. Chem. 46 2003 3476
10. S.T. Wrobleski, P. Chen, J. Hynes Jr., S. Lin, D.J. Norris, C.R. Pandit, S. Spergel, H. Wu, J.S. Tokarski, X. Chen, K.M. Gillooly, P.A. Kiener, K.W. McIntyre, V. Patil-koota, D.J. Shuster, L.A. Turk, G. Yang, and K. Leftheris J. Med. Chem. 46 2003 2110
11. For the synthesis of indazole derivatives, see A.Y. Lebedev, A.S. Khartulyari, and A.Z. Voskoboynikov J. Org. Chem. 70 2005 596
12. L.D. Shirtcliff, T.J.R. Weakley, M.M. Haley, F. Kohler, and R. Herges J. Org. Chem. 69 2004 6979
13. J.C. Antilla, J.M. Baskin, T.E. Barder, and S.L. Buchwald J. Org. Chem. 69 2004 5578
14. M. Cheung, A. Boloor, and J.A. Stafford J. Org. Chem. 68 2003 4093
15. E.M. Isin, M. de Jonge, and N. Castagnoli Jr. J. Org. Chem. 66 2001 4220
16. J.-H. Sun, C.A. Teleha, J.-S. Yan, J.D. Rodgers, and D.A. Nugiel J. Org. Chem. 62 1997 5627
17. J.J. Song, and N.K. Yee Org. Lett. 2 2000 519
18. A. Alberti, N. Bedogni, M. Benaglia, R. Leardini, D. Nanni, G.F. Pedulli, A. Tundo, and G. Zanardi J. Org. Chem. 57 1992 607
19. J.H. Lee, A. Matsumoto, M. Yoshida, and O. Simamura Chem. Lett. 1974 951
20. K.Y. Lee, J.M. Kim, and J.N. Kim Tetrahedron Lett. 44 2003 6737
21. For DDQ oxidation, see P. Muller, and J. Rocek J. Am. Chem. Soc. 94 1972 2716
22. F. Stoos, and J. Rocek J. Am. Chem. Soc. 94 1972 2719
23. R.P. Thummel, W.E. Cravey, and D.B. Cantu J. Org. Chem. 45 1980 1633
24. F. Wurche, W. Sicking, R. Sustmann, F.-G. Klarner, and C. Ruchardt Chem. Eur. J. 10 2004 2707 and references cited therein
25. For hydroxylation and related oxidations with DDQ, see Y.-C. Xu, E. Lebeau, J.W. Gillard, and G. Attardo Tetrahedron Lett. 34 1993 3841
26. F.D. Ramdayal, D.J. Kiemle, and R.T. LaLonde J. Org. Chem. 64 1999 4607
27. Z. Zhang, and G. Magnusson J. Org. Chem. 61 1996 2394
28. E.J. Corey, and Y.B. Xiang Tetrahedron Lett. 28 1987 5403
29. K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, and T. Horaguchi J. Chem. Soc., Perkin Trans. 1 2001 3230
30. For the synthesis of Baylis-Hillman adducts of cyclic enones, see S. Luo, X. Mi, H. Xu, P.G. Wang, and J.-P. Cheng J. Org. Chem. 69 2004 8413
31. K.Y. Lee, J.H. Gong, and J.N. Kim Bull. Korean Chem. Soc. 23 2002 659
32. K.Y. Lee, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 45 2004 5485
33. A. Patra, S. Batra, B.S. Joshi, R. Roy, B. Kundu, and A.P. Bhaduri J. Org. Chem. 67 2002 5783
34. V.K. Aggarwal, D.K. Dean, A. Mereu, and R. Williams J. Org. Chem. 67 2002 510
35. 3) δ 1.63 (s, 9H), 6.93-6.99 (m, 1H), 7.16 (dt, J = 8.4 and 0.9 Hz, 1H), 7.23-7.29 (m, 1H), 7.39-7.51
36. For the mechanism of carbazole synthesis, see: R.J. Sundberg A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon Oxford 119 206