A facile synthesis of pyrazolines from Baylis-Hillman adducts

Chemistry Letters

Volumn 37, Issue 6, 2008, Pages 624-625

  Yadav, J S ^a   Singh, A P ^a   Bhunia, D C ^a   Basak, A K ^a   Srihari, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 48249099694     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.624     Document Type: Article

References (26)

1. a) K. Y. Lee, J. N. Kim, J. M. Kim, Tetrahedron Lett. 2003, 44, 6131.
2. b) K. Y. Lee, J. M. Kim, J. N. Kim, Tetrahedron 2003, 59, 385.
3. c) Y. J. Im, K. Y. Lee, T. H. Kim, J. N. Kim, Tetrahedron Lett. 2002, 43, 4675.
4. a) J. N. Kim, J. M. Kim, K. Y. Lee, Synlett 2003, 821.
5. b) J. N. Kim, H. S. Kim, J. H. Gong, Y. M. Chung, Tetrahedron Lett. 2001, 42, 8341.
6. a) S. E. Drewes, N. D. Emslie, J. Chem. Soc., Perkin Trans. 1 1982, 2079.
7. b) H. M. R. Hoffmann, J. Rabe, Helv. Chim. Acta 1984, 67, 413.
8. c) H. M. R. Hoffmann, J. Rabe, J. Org. Chem. 1985, 50, 3849.
9. a) H. M. R. Hoffmann, J. Rabe, Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
10. b) R. Buchholz, H. M. R. Hoffmann, Helv. Chim. Acta 1991, 74, 1213.
11. c) F. Ameer, S. E. Drewes, R. Hoole, P. T. Kaye, A. T. Pitchford, J. Chem. Soc., Perkin Trans. 1 1985, 2713.
12. D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811.
13. D. Nauduri, G. D. Reddy, Chem. Pharm. Bull. (Tokyo) 1998, 46, 1254.
14. S. S. Korgaokar, P. H. Patil, M. T. Shah, H. M. Parekh, Indian Pharm. Sci. 1996, 58, 222.
15. J. H. Ahn, H. M. Kim, S. H. Jung, S. K. Kang, K. R. Kim, S. D. Rhee, S. D. Yang, H. G. Cheon, S. S. Kim, Bioorg. Med. Chem. Lett. 2004, 14, 4461.
16. R. H. Udupi, A. R. Kushnoor, A. R. Bhat, Indian J. Heterocycl. Chem. 1998, 8, 63.
17. A. A. Bilgin, E. Paska, R. Sunal, Arzneim.-Forsch. 1993, 43, 1041.
18. a) M. A. Ali, M. S. Yar, M. Kumar, G. S. Pandian, Nat. Prod. Res. 2007, 21, 575.
19. b) S. G. Kucukguzel, S. Rollas, Farmaco 1975, 64, 1075.
20. c) Ş. G. Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A. C. Ekinci, A. Vidin, Eur. J. Med. Chem. 2000, 35, 761.
21. d) A. A. Santilli, D. H. Kim, F. J. Gregory, J. Pharm. Sci. 1975, 64, 1057.
22. e) M. Shaharyar, A. A. Siddiqui, M. A. Ali, D. Sriram, P. Yogeeswari, Bioorg. Med. Chem. Lett. 2006, 16, 3947.
23. f) M. Shaharyar, A. A. Siddiqui, M. A. Ali, Bioorg. Med. Chem. Lett. 2006, 16, 4571.
24. g) M. A. Ali, M. Shaharyar, A. A. Siddiqui, Eur. J. Med. Chem. 2007, 42, 268.
25. In two-step sequence, isolated yields of the oxidized Baylis-Hillman adducts were found to be low. This may be attributed towards the high reactivity of the oxidized product of Baylis-Hillman adducts.
26. 4 and evaporated. The crude reaction mixture was purified by column chromatography using hexane:ethyl acetate (9:1) as eluent to afford pure pyrazolines.