Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 6863-6871

  Dahlén, Kristian ^a   Wallén, Erik A A ^a,b   Grøtli, Morten ^a   Luthman, Kristina ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; BROMINE COMPOUNDS; DERIVATIVES; POLYPEPTIDES; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BIOLOGICAL ACTIVITIES; CHROMONE STRUCTURES; HYDROXY GROUPS; HYDROXYL GROUPS;

KETONES;

8 BROMO 6 CHLORO 3 HYDROXYCHROMONE DERIVATIVE; ALKYL GROUP; BROMINE DERIVATIVE; CHROMONE DERIVATIVE; FLAVONOID; HYDROXYL GROUP; PALLADIUM; PEPTIDE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HECK REACTION; QUANTUM YIELD; REACTION ANALYSIS; SONOGASHIRA REACTION; STILLE REACTION; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

CHEMISTRY, ORGANIC; CHROMONES; CROSS-LINKING REAGENTS; FLAVONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 33750452718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061008f     Document Type: Article

References (58)

1. Harborne, J. B.; Williams, C. A. Photochemistry 2000, 55, 481-504.
2. Havsteen, B, H. Pharmacol. Ther. 2002, 96, 67-202.
3. Birt, D. F.; Hendrich, S.; Wang, W. Pharmacol. Ther. 2001, 90, 157-177.
4. López-Lázaro, M. Curr. Med. Chem - Anti-Cancer Agents 2002, 2, 691-714.
5. Pouget, C.; Lauthier, F.; Simon, A.; Fagnere, C.; Basly, J.-P.; Delage, C.; Chulia, A.-J. Bioorg. Med. Chem. Lett. 2001, 11, 3095-3097.
6. Zheng, X.; Meng, W. D.; Xu, Y. Y.; Cao, J. G.; Qing, F. L. Bioorg. Med. Chem. Lett. 2003, 13, 881-884.
7. Gobbi, S.; Rampa, A.; Bisi, A.; Belluti, F.; Piazzi, L.; Valenti, P.; Caputo, A.; Zampiron, A.; Carrara, M. J. Med. Chem. 2003, 46, 3662-3669.
8. Atassi, G.; Briet, P.; Berthelon, J. J.; Collonges, F. Eur. J. Med. Chem. 1985, 20, 393-402.
9. Yu, D.; Chen, C. H.; Brossi, A.; Lee, K. H. J. Med. Chem. 2004, 47, 4072-4082.
10. Hu, C.; Chen, K.; Shi, Q.; Kilkuskie, R. E.; Chen, Y.; Lee, K. H. J. Nat. Prod. 1994, 57, 42-51.
11. Ungwitayatorn, J.; Samee, W.; Pimthon, J. J. Mol. Struct. 2004, 689, 99-106.
12. Burda, S.; Oleszek, W. J. Agric. Food Chem 2001, 49, 2774-2779.
13. Rackova, L.; Firakova, S.; Kostalova, D.; Stefek, M.; Sturdik, E.; Majekova, M. Bioorg. Med. Chem. 2005, 13, 6477-6484.
14. Soobrattee, M. A.; Neergheen, V. S.; Luximon-Ramma, A.; Aruoma, O. I.; Bahorun, T. Mutat. Res. 2005, 579, 200-213.
15. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930.
16. Dahlén, K.; Grøtli, M.; Luthman, K. Understanding Biology Using Peptides; Blondelle, S., Ed.; American Peptide Society: San Diego, 2006; pp 677-678.
17. Sengupta, P. K.; Kasha, M. Chem. Phys. Lett. 1979, 68, 382-385.
18. Swinney, T. C.; Kelley, D. F. J. Chem. Phys. 1993, 99, 211-221.
19. Mcmorrow, D.; Kasha, M. J. Phys. Chem. 1984, 88, 2235-2243.
20. Klymchenko, A. S.; Demchenko, A. P. J. Am. Chem. Soc. 2002, 124, 12372-12379.
21. Klymchenko, A. S.; Mely, Y. Tetrahedron Lett. 2004, 45, 8391-8394.
22. Klymchenko, A. S.; Avilov, S. V.; Demchenko, A. P. Anal. Biochem. 2004, 329, 43-57.
23. Bondar, O. P.; Pivovarenko, V. G.; Rowe, E. S. Biochim. Biophys. Acta Biomembr. 1998, 1369, 119-130.
24. Klymchenko, A. S.; Duportail, G.; Ozturk, T.; Pivovarenko, V. G.; MeIy, Y.; Demchenko, A. P. Chem. Biol. 2002, 9, 1199-1208.
25. Costa, A. M. B. S. R. C. S.; Dean, F. M.; Jones, M. A.; Smith, D. A. Chem. Commun. 1983, 1098-1099.
26. Flynn, D. G.; Robertson, A. J. Chem. Soc. 1936, 215-217.
27. Fillol, L.; Martinezutrilla, R.; Miranda, M. A.; Morera, I. M. Heterocycles 1989, 29, 511-520.
28. Da Re, P.; Verlicchi, L. Arch. Pharm. 1963, 296, 714-717.
29. Dare, P.; Cimatori. L Experientia 1962, 18, 67-68
30. Dahlén, K.; Grøtli, M.; Luthman, K. Synlett 2006, 897-900.
31. Bhadange, R. E.; Doshi, A. G.; Raut, A. W. Asian J. Chem. 2002, 14, 509-511.
32. Mazumdar, A. K. D.; Karmakar, P. K.; Rahman, M.; Saha, G. C.; Rangachari, K.; Banerji, K. D. J. Indian Chem. Soc. 1992, 69, 207-209.
33. Sosnovskikh, V. Y. Russ. Chem. Rev. 2003, 72, 489-516.
34. Zheng, X.; Cao, J. G.; Meng, W. D.; Qing, F. L. Bioorg. Med. Chem. Lett. 2003, 13, 3423-3427.
35. Costa, A. M. B. S. R. C. S.; Dean, F. M.; Jones, M. A.; Varma, R. S. J. Chem. Soc., Perkin Trans. 1 1985, 799-808.
36. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486.
37. Ritter, K. Synthesis 1993, 735-762.
38. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
39. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
40. Davis, F. A.; Chen, B. C. J. Org. Chem. 1993, 58, 1751-1753.
41. Ali, S. M.; Ilyas, M. J. Org. Chem. 1986, 51, 5415-5417.
42. Utale, P. S.; Ranghuwanshi, P. B.; Doshi, A. G. Asian J. Chem. 1999, 11, 644-646.
43. Bennett, C. J.; Caldwell, S. T.; McPhail, D. B.; Morrice, P. C.; Duthie, G. G.; Hartley, R. C. Bioorg. Med. Chem. 2004, 12, 2079-2098.
44. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. 1994, 33, 2379-2411.
45. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
46. Hesse, S.; Kirsch, G. Tetrahedron Lett. 2003, 44, 97-99.
47. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
48. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216.
49. Chekulaeva, I. A.; Kondrat'eva, L. V. Russ. Chem. Rev. 1965, 34, 1583-1606.
50. The previously reported syntheses of 28 and 37 were not repeated with microwave heating due to previously satisfying yields using thermal heating.
51. Kamino, T.; Kuramochi, K.; Kobayashi, S. Tetrahedron Lett. 2003, 44, 7349-7351.
52. Haaseheld, M.; Hatzis, M.; Mann, J. J. Chem Soc. Perkin Trans. 1 1993, 2907-2911
53. 4 salt which is more stable and easier to handle than the phosphine itself. This phosphine is activated when base is added.
54. Compound 55 could easily be deacetylated using NaOMe in MeOH to obtain 58 in excellent yield (>98%).
55. Deprotection of the phthalimide group in 37 was performed using ethylenediamine in refluxing ethanol for 5 h. The primary amine was not isolated but instead reacted with di-tert-butyl dicarbonate in MeOH/THF at reflux for 14 h to obtain the Boc-protected amine 52 (87%).
56. Banerji, K. D.; Poddar, D. J. Indian Chem. Soc. 1979, 56, 62-65.
57. Thool, A. W.; Ghiya, B. J. J. Indian Chem. Soc. 1988, 65, 522-524.
58. Sandulache, A.; Cascaval, A.; Toniutti, N.; Giumanini, A. G. Tetrahedron 1997, 53, 9813-9822.