Aqueous-phase Suzuki-Miyaura cross-coupling reactions of free halopurine bases

Synthesis

Volumn , Issue 20, 2006, Pages 3515-3526

  Čapek, Petr ^a   Vrábel, Milan ^a   Hasník, Zbyněk ^a   Pohl, Radek ^a   Hocek, Michal ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Boronic acids; Cross coupling reactions; Microwaves; Purines; Water

Indexed keywords

ACETONITRILE; CHEMICAL MODIFICATION; IRRADIATION; MICROWAVES; MIXTURES; PURIFICATION;

BORONIC ACIDS; MICROWAVE IRRADIATION; PURINES; REACTION MIXTURE; SUZUKI-MIYAURA CROSS-COUPLING REACTIONS;

CARBOXYLIC ACIDS;

2 (3 PYRIDYL)ADENINE; 2 (4 METHOXYPHENYL)ADENINE; 2 AMINO 6 (3 NITROPHENYL) 9H PURINE; 2 AMINO 6 (3 PYRIDYL) 9H PURINE; 2 AMINO 6 (4 METHOXYPHENYL) 9H PURINE; 2 AMINO 6 PHENYL 9H PURINE; 2 ARYLPURINE DERIVATIVE; 2 CHLOROADENINE; 2 PHENYLADENINE; 2,6 DICHLORO 9H PURINE; 6 (2 THIENYL) 9H PURINE; 6 (3 AMINOPHENYL) 9H PURINE; 6 (3 NITROPHENYL) 9H PURINE; 6 (3 PYRIDYL) 9H PURINE; 6 (3 THIENYL) 9H PURINE; 6 (4 FLUOROPHENYL) 9H PURINE; 6 (4 METHOXYPHENYL) 9H PURINE; 6 (4 PYRIDYL) 9H PURINE; 6 ARYLPURINE DERIVATIVE; 6 PHENYL 9H PURINE; 8 (3 NITROPHENYL)ADENINE; 8 (3 PYRIDYL)ADENINE; 8 (4 METHOXYPHENYL)ADENINE; 8 ARYLPURINE DERIVATIVE; 8 PHENYLADENINE; ALKENYLBORONIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; HALOPURINE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOLOGICAL ACTIVITY; CROSS COUPLING REACTION; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; SUZUKI REACTION;

EID: 33750591498     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950240     Document Type: Article

References (54)

1. Reviews: (a) Legraverend, M.; Grierson, D. S. Bioorg. Med. Chem. 2006, 14, 3987.
2. (b) Strouse, J. J.; Jeselnik, M.; Arterburn, J. B. Acta Chim. Slov. 2005, 52, 187.
3. (a) Hocek, M.; Holy, A.; Votruba, I.; Dvořáková, H. J. Med. Chem. 2000, 43, 1817.
4. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. Collect. Czech. Chem. Commun. 2001, 66, 483.
5. Hocek, M.; Nau, P.; Pohl, R.; Votruba, I.; Furman, P. A.; Tharnish, P. M.; Otto, M. J. J. Med. Chem. 2005, 48, 5869.
6. (a) Bakkestuen, A. K.; Gundersen, L.-L.; Langli, G.; Liu, F.; Nolsøe, J. M. J. Bioorg. Med. Chem. Lett. 2000, 10, 1207.
7. (b) Andresen, G.; Gundersen, L.-L.; Nissen-Meyer, J.; Rise, F.; Spilsberg, B. Bioorg. Med. Chem. Lett. 2002, 12, 567.
8. (c) Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, B. J. Med. Chem. 2002, 45, 1383.
9. (d) Bakkestuen, A. K.; Gundersen, L.-L.; Utenova, B. T. J. Med Chem. 2005, 48, 2710.
10. Cocuzza, A. J.; Chidester, D. R.; Culp, S.; Fitzgerald, L.; Gilligan, P. Bioorg. Med. Chem. Lett. 1999, 9, 1063.
11. Wan, Z.; Boehm, J. C.; Bower, M. J.; Kassis, S.; Lee, J. C.; Zhao, B.; Adams, J. L. Bioorg. Med. Chem. Lett. 2003, 13, 1191.
12. Vandromme, L.; Piguel, S.; Lozach, O.; Meijer, L.; Legraverend, M.; Grierson, D. S. Bioorg. Med. Chem. Lett. 2006, 16, 3144.
13. (a) Cristalli, G.; Lambertucci, C.; Taffi, S.; Vittori, S.; Volpini, R. Curr. Top. Med. Chem. 2003, 3, 387.
14. (b) Müller, C. E. Curr. Top. Med. Chem. 2003, 3, 445.
15. (c) Kim, Y. C.; Ji, X.; Melman, N.; Linden, J.; Jacobson, K. A. J. Med. Chem. 2000, 43, 1165.
16. (d) Kim, S. A.; Marshall, M. A.; Melman, N.; Kim, H. S.; Müller, C. E.; Linden, J.; Jacobson, K. A. J. Med. Chem. 2002, 45, 2131.
17. (e) Baraldi, P. G.; Tabrizi, M. A.; Preti, D.; Bovero, A.; Fruttarolo, F.; Romagnoli, R.; Moorman, A. R.; Gessi, S.; Merighi, S.; Varani, K.; Borea, P. A. Bioorg. Med. Chem. Lett. 2004, 14, 3607.
18. Chang, L. C. W.; Spanjersberg, R. F.; von Frijtag Drabbe Kunzel, J. K.; Mulder-Krieger, T.; Brussee, J.; IJzerman, A. P. J. Med. Chem. 2006, 49, 2861.
19. (a) He, H.; Zatorska, D.; Kim, J.; Aguirre, J.; Llauger, L.; She, Y.; Wu, N.; Immormino, R. M.; Gewirth, D. T.; Chiosis, G. J. Med. Chem. 2006, 49, 381.
20. (b) Vilenchik, M.; Solit, D.; Basso, A.; Huezo, H.; Lucas, B.; He, H.; Rosen, N.; Spampinato, C.; Modrich, P.; Chiosis, G. Chem. Biol. 2004, 11, 787.
21. Reviews: (a) Hocek, M. Eur. J. Org. Chem. 2003, 245.
22. (b) Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875.
23. (c) Lakshman, M. K.J. Organomet. Chem. 2002, 653, 234.
24. (a) Havelková, M.; Hocek, M.; Česnek, M.; Dvořák, D. Synlett 1999, 1145.
25. (b) Havelková, M.; Dvořák, D.; Hocek, M. Synthesis 2001, 1704.
26. (a) Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779.
27. (b) Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479.
28. (c) Gunda, P.; Russon, L. M.; Lakshman, M. K. Angew. Chem. Int. Ed. 2004, 43, 6372.
29. (d) Lakshman, M. K.; Gunda, P.; Prandhan, P. J. Org. Chem. 2005, 70, 10329.
30. (e) Liu, J.; Robins, M. J. Org. Lett. 2004, 6, 3421.
31. (f) Liu, J.; Robins, M. J. Org. Lett. 2005, 7, 1149.
32. (a) Hocek, M.; Dvořáková, H. J. Org. Chem. 2003, 68, 5773.
33. (b) Ding, S.; Gray, N. S.; Ding, Q.; Schultz, P. G. Tetrahedron Lett. 2001, 42, 8751.
34. (a) Amann, N.; Wagenknecht, H.-A. Synlett 2002, 687.
35. (b) Amann, N.; Pandurski, E.; Fiebig, T.; Wagenknecht, H.-A. Chem. Eur. J. 2002, 8, 4877.
36. (c) Valis, L.; Wagenknecht, H.-A. Synlett 2005, 2281.
37. (a) Hocek, M.; Votruba, I.; Dvořáková, H. Tetrahedron 2003, 59, 607.
38. (b) Hocek, M.; Holy, A.; Dvořáková, H. Collect. Czech. Chem. Commun. 2002, 67, 325.
39. (c) Hocek, M.; Hocková, D.; Štambaský, J. Collect. Czech. Chem. Commun. 2003, 68, 837.
40. (d) Hocek, M.; Hocková, D.; Dvořáková, D. Synthesis 2004, 889.
41. (e) Hocek, M.; Pohl, R. Synthesis 2004, 2869.
42. General review on regioselective cross-couplings of di- and trihaloheterocycles, see: Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
43. Review, see: (a) Shaughnessy, K. H. Eur. J. Org. Chem. 2006, 1827.
44. Application to purine nucleosides, see: (b) Western, E. C.; Daft, J. R.; Johnson, E. M.; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem. 2003, 68, 6767.
45. Capek, P.; Hocek, M. Synlett 2005, 3005.
46. Capek, P.; Pohl, R.; Hocek, M. Org. Biomol. Chem. 2006, 4, 2278.
47. Hocek, M.; Holý, A.; Votruba, I.; Dvořáková, H. Collect. Czech. Chem. Commun. 2000, 65, 1683.
48. Estep, K. G.; Josef, K. A.; Bacon, E. R.; Carabateas, P. M.; Rumney, S.; Pilling, G. M.; Krafte, D. S.; Volberg, W. A.; Dillon, K.; Dugrenier, N.; Briggs, G. M.; Canniff, P. C.; Gorczyca, W. P.; Stankus, G. P.; Ezrin, A. M. J. Med. Chem. 1995, 38, 2582.
49. Bråthe, A.; Gundersen, L.-L.; Rise, F.; Eriksen, A. B.; Vollsnes, A. V.; Wang, L. Tetrahedron 1999, 55, 211.
50. Chin, A.; Hung, M.-H.; Stock, L. M. J. Org. Chem. 1981, 46, 2203.
51. Anderson, R. A.; Graves, D. J. Biochemistry 1973, 12, 1895.
52. Taylor, E. C.; Morrison, R. W. Jr. J. Am. Chem. Soc. 1965, 87, 1976.
53. Taylor, E. C.; Vogl, C.; Cheng, C. C. J. Am. Chem. Soc. 1959, 81, 2442.
54. Kos, N. J.; van der Plas, H. C. J. Org. Chem. 1980, 45, 2942.