Microwave-assisted, boron trichloride mediated acylation of phenols - Synthesis of (o-hydroxyaryl)(aryl)methanones and xanthones

Journal of Combinatorial Chemistry

Volumn 8, Issue 3, 2006, Pages 361-367

  Zhang, Lei ^a   Zhang, John Y ^a  

^a CytRx Laboratories Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; BORANE DERIVATIVE; BORON TRICHLORIDE; CHLORIDE; DRUG DERIVATIVE; METHANE; PHENOL DERIVATIVE; XANTHONE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

ACYLATION; BENZOPHENONES; BORANES; CHLORIDES; COMBINATORIAL CHEMISTRY TECHNIQUES; METHANE; MICROWAVES; MODELS, CHEMICAL; PHENOLS; XANTHONES;

EID: 33744466600     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0501007     Document Type: Article

References (58)

1. (a) Ortholand, J.; Ganesan, A. Curr. Opin. Chem. Biol. 2004, 8, 271.
2. (b) Boldi, A. M. Curr. Opin. Chem. Biol. 2004, 8, 281.
3. (c) Zou, N.; Liu, J. F.; Jiang, B. J. Comb. Chem. 2003, 5, 754.
4. (d) Makino, S.; Okuzumi, T.; Tsuji, T.; Nakanishi, E. J. Comb. Chem. 2003, 5, 756.
5. (e) Husemoen, G.; Olsson, R.; Andersson, C. M.; Harvey, S. C.; Hansen, H. C. J. Comb. Chem. 2003, 5, 606.
6. (a) Dolle, R. E. J. Comb. Chem. 2004, 6, 623.
7. (b) Dolle, R. E. J. Comb. Chem. 2003, 5, 693.
8. (c) Dolle, R. E. J. Comb. Chem. 2002, 4, 369.
9. (d) Dolle, R. E. J. Comb. Chem. 2001, 3, 477.
10. (e) Dolle, R. E. J. Comb. Chem. 2000, 2, 383.
11. (f) Dolle, R. E.; Nelson, K. H. J. Comb. Chem. 1999, 1, 235.
12. (g) Dolle, R. E. Mol. Diversity 1998, 3, 199.
13. (a) Plunkett, M. J.; Ellman, J. A. Sci. Am. 1997, 276, 68.
14. (b) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613.
15. (c) Ellman, J. A.; Thompson, L. A. Chem. Rev. 1996, 96, 555.
16. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
17. (d) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233.
18. Zhang, L.; Zhang, J. J. Comb. Chem. 2005, 7, 622.
19. For detailed biological activity and therapeutic information of (o-Hydroxyaryl)(aryl)methanone based drugs, please consult (a) Merck Index; Merck & Co., Inc.: Rahway, NJ.
20. (b) Breitenlechner, C. B.; Friebe, W.; Brunet, E.; Werner, G.; Graul, K.; Thomas, U.; Kunkele, K.; Schafer, W.; Gassel, M.; Bossemeyer, D.; Huber, R.; Engh, R. A.; Masjost, B. J. Med. Chem. 2005, 48, 163.
21. (c) Chao, S. H.; Price, D. H. J. Biol. Chem. 2001, 276, 31793.
22. (d) Takada, Y.; Aggarwall, B. B. J. Biol. Chem. 2004, 279, 4750.
23. For recent application of Friedel-Crafts-type reactions, see the following for reference: (a) Dehmlow, H.; Aebi, J. D.; Jolodon, S.; Ji, Y. H.; von der Mark, E. M.; Himber, J.; Morand, O. H. J. Med. Chem. 2003, 46, 3354.
24. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219.
25. Toyoda, T.; Sasakura, K.; Sugasawa, T. J. Org. Chem. 1981, 46, 189.
26. For acyl chloride and organoboronic acid coupling, see the following for reference: (a) Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057.
27. (b) Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109.
28. For Cu(I) mediated thioester with organostannanes or boronic acids couplings, please see the following for reference: (a) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
29. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
30. (c) Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554.
31. For coupling of bromomagnesium phenolates and acyl chlorides to give ortho carbonylation, see reference and references cited in the following paper: Bigi, F.; Caairaghi, G.; Casnati, G.; Marchesi, S.; Sartori, G. Tetrahedron 1984, 40, 4081.
32. For previous work of Lewis acid mediated phenol coupling with acyl chlorides and isocyanates, please read the following references: (a) Piccolo, O.; Filippini, L.; Tinucci, L.; Valoti, E.; Citterio, A. Tetrahedron 1986, 42, 885.
33. (b) Balduzzi, G.; Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. Synthesis 1982, 879.
34. (c) Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. J. Chem. Soc., Perkin Trans. 1 1984, 2655.
35. (d) Bigi, F.; Casiraghi, G.; Casnati, G.; Marchesi, S.; Sartori, G.; Vignali, C. Tetrahedron 1984, 40, 4081.
36. For reviews covering recent microwave-mediated synthesis progress and its applications, please read the following references: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
37. (b) Hayes, B. L. Aldrichimica Acta 2004, 37, 66.
38. (c) Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128.
39. (d) Mavanadadi, F.; Lidström, P. Curr. Topics Med. Chem. 2004, 4, 773.
40. (e) Al-Obeidi, F.; Austin, R. E.; Okonya, J. F.; Bond, D. R. S. Mini-Rev. Med. Chem. 2003, 3, 449.
41. (f) Wilson, N. S.; Roth, G. P. Curr. Opin. Drug Discovery Dev. 2002, 5, 620-629.
42. (g) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
43. For detailed biological activity information of xanthones, please consult (a) Merck Index; Merck & Co., Inc.: Rahway, NJ.
44. (b) Tozer, G. M.; Kanthou, C.; Baguley, B. C. Nat. Rev. Cancer 2005, 5, 423.
45. (c) Tisdale, E. J.; Kochman, D. A.; Theodorakis, E. A. Tetrahedron Lett. 2003, 44, 3281.
46. (d) Ho, C. K.; Huang, Y. L.; Chen, C. C. Planta Med. 2002, 68, 975.
47. (e) Jinstart, W.; Ternal, B.; Buddhasukh, D.; Polya, G. M. Phytochemistry 1992, 31, 3711.
48. (f) Kelly, J. X.; Winter, R.; Peyton, D. H.; Hinrich, D. J.; Riscoe, M. Antimicrob. Agents Chemother. 2002, 46, 144.
49. (g) Jiang, D. J.; Dai, Z.; Li, Y. J. Cardiovasc. Drug Rev. 2004, 22, 91.
50. (h) Nakatani, K.; Nakahata, N.; Arakawa, T.; Yasuda, H.; Ohizumi, Y. Biochem. Pharmacol. 2002, 63, 73.
51. (i) Ahmad, V. U.; Rahman, I.; Khan, M. A.; Arfan, M.; Siddiqui, M. T. Z. Naturforsch. 2002, 57B, 122.
52. (j) Pinto, M. M.; Sousa, M. E.; Nascimento, M. S. Curr. Med. Chem. 2005, 12, 2517.
53. (k) Riscoe, M.; Kelly, J. X.; Winter, R. Curr. Med. Chem. 2005, 12, 2539.
54. For previous syntheses of xanthones, please consult (a) Silva, A. M.; Pinto, D. C. Curr. Med. Chem. 2005, 12, 2481 and references therein.
55. (b) Recanatini, M.; Bisi, A.; Cavalli, A.; Belluti, F.; Gobbi, S.; Rampa, A.; Valenti, P.; Palzer, M.; Palusczak, A.; Hartmann, R. W. J. Med. Chem. 2001, 44, 672.
56. (c) Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 4273 and references therein.
57. For references of Houben-Hoesche reaction, please see the following for reference: Olah, G. A. Friedel Crafts and Related Reactions; Wiley-Interscience: New York, 1964; Vol. III, Part 1, p 383.
58. Colclough, T.; Gerrard, W.; Lappert, M. F. J. Chem. Soc. 1955, 907.