Silica gel supported InBr 3 and InCl 3: New catalysts for the facile and rapid oxidation of 2′-hydroxychalcones and flavanones to their corresponding flavones under solvent free conditions

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 253-256

  Ahmed, Naseem ^a   Ali, Hasrat ^a   Van Lier, Johan E ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

1,4 Cycloaddition; 2 Hydroxychalcones; Flavanone; Flavone; Silica gel supported InBr 3 and InCl 3

Indexed keywords

BROMINE DERIVATIVE; CHALCONE DERIVATIVE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; SILICA GEL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 10044290884     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.062     Document Type: Article

References (44)

1. H.-W. Chu, H.-T. Wu, and Y.-J. Lee Tetrahedron 60 2004 2647 2655
2. Y. Isogi, Y. Komoda, and T. Okamoto Chem. Pharm. Bull. 18 1970 1872
3. R.B. Gamill, C.E. Day, and P.E. Schurr J. Med. Chem. 26 1983 1672
4. A. Yamashita J. Am. Chem. Soc. 107 1985 5823
5. W.H. Gerwick J. Nat. Prod. 52 1989 252
6. J. Ferté, J.-M. Kühnel, G. Chapuis, Y. Rolland, G. Lewin, and M.A. Schwaller J. Med. Chem. 42 1999 478
7. K. Lewis, F.R. Stermitz, and F. Collins Proc. Natl. Acad. Sci. U.S.A. 97 2000 1433
8. J.B. Harborne The Flavonoids, Advances in Research Since 1986 1993 Chapman and Hall London
9. M.G. Block Nutr. Rev. 50 1992 207 213
10. M.G. Herlog, and E.J.M. Festens Lancet 342 1993 1007 1011
11. Y. Seimbille, H. Ali, and J.E. van Lier J. Chem. Soc., Perkin Trans. 1 2002 657
12. Y. Seimbille, F. Bénard, J. Rousseau, E. Pepin, A. Aliaga, G. Tessier, and J.E. van Lier Nucl. Med. Biol. 31 2004 691 698
13. H.S. Mahal, and K. Venkataraman J. Chem. Soc. 1935 866
14. H.S. Mahal, and K. Venkataraman J. Chem. Soc. 1936 569
15. H.H. Lee, and C.H. Tan J. Chem. Soc. 1965 2743
16. P.K. Bose, P. Chakrabarti, and A.K. Sanyal J. Indian Chem. Soc. 48 1971 1163
17. M.D.L. de la Torre, G.L. Marcorin, G. Pirri, A.C. Tomé, A.M.S. Silva, and J.A.S. Cavaleira Tetrahedron Lett. 43 2002 1689 1691
18. A.G. Doshi, P.A. Soni, and B.J. Ghiya Indian J. Chem. 25B 1986 759
19. J.K. Makrandi, and Seema Chem. Ind. 1989 607
20. K. Imafuku, M. Honda, and J.F.W. McOmie Synthesis 1987 199
21. N. Hans, and S.K. Grover Synth. Commun. 23 1993 1021 1023
22. U.K. Mallik, M.M. Saha, and A.K. Mallik Indian J. Chem. 28B 1989 970
23. S. Gobbi, A. Rampa, A. Bisi, F. Belluti, L. Piazzi, P. Valent, A. Caputo, A. Zampiron, and M. Carrara J. Med. Chem. 46 2003 3662 3669
24. M.D.L. De la Torre, G.L. Marcorin, G. Pirri, A.C. Tomé, A.M.S. Silva, and J.A.S. Cavaleiro Tetrahedron Lett. 43 2002 1689 1691
25. F.A.A. van Acker, J.A. Hageman, G.R.M.M. Haenen, W.J.F. van der Vijgh, A. Bast, and W.M.P.B. Menge J. Med. Chem. 43 2000 3752 3760
26. M.E. Zwaagstra, H. Timmerman, A.C. van de Stolpe, F.J.J. de Kanter, M. Tamura, Y. Wada, and M.-Q. Zhang J. Med. Chem. 41 1998 1428 1438
27. T. Akama, Y. Shida, T. Sugaya, H. Ishida, K. Gomi, and M. Kasai J. Med. Chem. 39 1996 3461 3469
28. J.R. Pfister, W.E. Wymann, M.E. Schuler, and A.P. Roszkowski J. Med. Chem. 23 1980 335 338
29. S.-H. Jung, S.-H. Cho, T.H. Dang, J.-H. Lee, J.-H. Ju, M.-K. Kim, S.-H. Lee, J.-C. Ryu, and Y. Kim Eur. J. Med. Chem. 38 2003 537 545
30. H. Miyake, E. Takizawa, and M. Sasaki Bull. Chem. Soc. Jpn. 76 2003 835 836
31. C.J. Li, and T.H. Chan Tetrahedron 55 1999 11149
32. G. Babu, and P. Perumal Aldrichim. Acta 33 2000 16
33. N. Sakai, K. Annaka, and T. Konakahara Org. Lett. 6 2004 1527 1530
34. K.H. Kumar, D. Muralidharan, and P.T. Perumal Synthesis 1 2004 63 68
35. T. Miyai, K. Inoue, M. Yasuda, I. Shibata, and A. Baba Tetrahedron Lett. 39 1998 1929 1932
36. J.S. Yadav, B.V. Reddy, A.K. Raju, and C.V. Rao Tetrahedron Lett. 43 2002 5437
37. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and G. Parimala Synthesis 15 2003 2390 2394
38. N. Ahmed, and W.H. Ansari J. Chem. Res. Synop. 9 2003 572 573
39. 3 (14-19 mg) dissolved in a minimum amount of acetonitrile is added to silica gel (1.0 g), evaporated to dryness as above, and stored under argon for further use
40. +) (70%), 257 (M-Cl) (100%), 222 (M-2Cl) (25%), 195, 166
41. L. Yin, Z.-H. Zhang, Y.-M. Wang, and M.-L. Pang Synlett 10 2004 1727 1730
42. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025
43. R.S. Varma Green Chem. 1 1999 43
44. V. Krchnak, and M.W. Holladay Chem. Rev. 102 2002 61