Regioselectivity in cross-coupling reactions of 2,6,8-trichloro-9- (tetrahydropyran-2-yl)purine: Synthesis of 2,6,8-trisubstituted purine bases

Synthesis

Volumn , Issue 17, 2004, Pages 2869-2876

  Hocek, Michal ^a   Pohl, Radek ^a  

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

Author keywords

Cross coupling reactions; Iron; Nucleobases; Palladium; Purines

Indexed keywords

CATALYSTS; ISOMERS; MIXTURES; NUCLEAR MAGNETIC RESONANCE; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING REACTIONS; FACILE IDENTIFICATION; PURINE RING; REGIOSELECTIVITY;

REACTION KINETICS;

2 CHLORO 6,8 DIMETHYL 9 (TETRAHYDROPYRAN 2 YL)PURINE; 2,6 DICHLORO 6 PHENYL 9 (TETRAHYDROPYRAN 2 YL)PURINE; 2,6,8 TRICHLORO 9 (TETRAHYDROPYRAN 2 YL)PURINE; 2,8 DICHLORO 6 PHENYL 9 (TETRAHYDROPYRAN 2 YL)PURINE; BENZENEBORONIC ACID; CARBON; IRON; NUCLEIC ACID BASE; ORGANOMETALLIC COMPOUND; PALLADIUM; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DEPROTECTION REACTION; ISOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 10644259620     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834881     Document Type: Article

References (50)

1. (a) Montgomery, J. A.; Hewson, K. J. Med. Chem. 1968, 11, 48.
2. (b) Parker, W. B.; King, S. A.; Allan, P. W.; Bennett, L. L. Jr.; Secrist, J. A.; Montgomery, J. A.; Gilbert, K. S.; Waud, W. R.; Wells, A. H.; Gillespie, G. Y.; Sorscher, E. J. Hum. Gene Ther. 1997, 8, 1637.
3. (c) Parker, W. B.; Allan, P. W.; Shaddix, S. C.; Rose, L. M.; Speegle, H. F.; Gillespie, G. Y.; Bennett, L. L. Jr. Biochem. Pharmacol. 1998, 55, 1673.
4. (d) Hassan, A. E. A.; Abou-Elkair, R. A. I.; Montgomery, J. A.; Secrist, J. A. III Nucleosides, Nucleotides, Nucleic Acids 2000, 19, 1123.
5. (a) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. J. Med. Chem. 2000, 43, 1817.
6. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. Collect. Czech. Chem. Commun. 2001, 66, 483.
7. (c) Andresen, G.; Gundersen, L.-L.; Nissen-Meyer, J.; Rise, F.; Spilsberg, B. Bioorg. Med. Chem. Lett. 2002, 12, 567.
8. (d) Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, D. J. Med. Chem. 2002, 45, 1383.
9. Hocek, M. Eur. J. Org. Chem. 2003, 245.
10. Hocek, M.; Holý, A.; Dvořáková, H. Collect. Czech. Chem. Commun. 2002, 67, 325.
11. Hocek, M.; Hocková, D.; Štambaský, J. Collect. Czech. Chem. Commun. 2003, 68, 837.
12. Hocek, M.; Dvořáková, H. J. Org. Chem. 2003, 68, 5773.
13. (a) Havelková, M.; Dvořák, D.; Hocek, M. Synthesis 2001, 1704.
14. (b) Hocek, M.; Votruba, I.; Dvořáková, H. Tetrahedron 2003, 59, 607.
15. Hocek, M.; Hocková, D.; Dvořáková, D. Synthesis 2004, 889.
16. (a) Havlíček, L.; Hanus, J.; Veselý, J.; Leclerc, S.; Meijer, L.; Shaw, G.; Strnad, M. J. Med. Chem. 1997, 40, 408.
17. (b) Legraverend, M.; Ludwig, O.; Bisagni, E.; Leclerc, S.; Meijer, L.; Bioorg. Med. Chem. Lett. 1998, 8, 793.
18. (c) Legraverend, M.; Ludwig, O.; Bisagni, E.; Leclerc, S.; Meijer, L.; Giocanti, N.; Sadri, R.; Favaudon, V. Bioorg. Med. Chem. 1999, 7, 1281.
19. (d) Gray, N. S.; Wodicka, L.; Thunnissen, A.-M. W. H.; Nornam, T. C.; Kwon, S.; Espinoza, F. H.; Morgan, D. O.; Barnes, G.; LeClerc, S.; Meijer, L.; Kim, S.-H.; Lockhart, D. J.; Schultz, P. G. Science 1998, 281, 533.
20. (e) Chang, Y.-T.; Gray, N. S.; Rosania, G. R.; Sutherlin, D. P.; Kwon, S.; Norman, T. C.; Sarohia, R.; Leost, M.; Meijer, L.; Schultz, P. G. Chem. Biol. 1999, 6, 361.
21. Verdugo, D. E.; Cancilla, M. T.; Ge, X.; Gray, N. S.; Chang, Y.-T.; Schultz, P. G.; Negishi, M.; Leary, J. A.; Bertozzi, C. R. J. Med. Chem. 2001, 44, 2683.
22. (a) Rosania, G. R.; Chang, Y.-T.; Perez, O.; Sutherlin, D.; Dong, H. L.; Lockhart, D. J.; Schultz, P. G. Nature Biotechnol. 2000, 18, 304.
23. (b) Chang, Y.-T.; Wignall, S. M.; Rosania, G. R.; Gray, N. S.; Hanson, S. R.; Su, A. I.; Merlie, J.; Moon, H. S.; Sangankar, S. B.; Perez, O.; Heald, R.; Schultz, P. G. J. Med. Chem. 2001, 44, 4497.
24. (c) Franěk, F.; Siglerová, V.; Havlíček, L.; Strnad, M.; Eckschlager, T.; Weigl, E. Collect. Czech. Chem. Commun. 2002, 67, 257.
25. Cocuzza, A. J.; Chidester, D. R.; Culp, S.; Fitzgerald, L.; Gilligan, P. Bioorg. Med. Chem. Lett. 1999, 9, 1063.
26. (a) Brill, W. K.-D.; Riva-Toniolo, C.; Müller, S. Synlett 2001, 1097.
27. (b) Brill, W. K.-D.; Riva-Toniolo, C. Tetrahedron Lett. 2001, 42, 6515.
28. (c) Ding, S.; Gray, N. S.; Ding, Q.; Schultz, P. G. Tetrahedron Lett. 2001, 42, 8751.
29. (d) Ding, S.; Gray, N. S.; Wu, X.; Ding, Q.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 1594.
30. (e) Brun, V.; Legraverend, M.; Grierson, D. S. Tetrahedron 2002, 58, 7911.
31. (f) Bork, J. T.; Lee, J. W.; Chang, Y.-T. QSAR Comb. Sci. 2004, 23, 245.
32. (a) Langli, G.; Gundersen, L.-L.; Rise, F. Tetrahedron 1996, 52, 5625.
33. (b) Nolsoe, J. M. J.; Gundersen, L.-L.; Rise, F. Acta Chem. Scand. 1999, 53, 366.
34. (a) Fischer, E. Ber. Dtsch. Chem. Ges. 1897, 30, 2220.
35. (b) Davoll, J.; Lowry, B. A. J. Am. Chem. Soc. 1951, 73, 2926.
36. Nolsøe, J. M. J.; Gundersen, L.-L.; Rise, F. Synth. Commun. 1998, 28, 4303.
37. (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609.
38. (b) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
39. (c) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2003, 42, 308.
40. (a) Havelková, M.; Hocek, M.; Česnek, M.; Dvořák, D. Synlett 1999, 1145.
41. (b) Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234.
42. (c) 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.
43. (a) Hirota, K.; Kitade, Y.; Kanbe, Y.; Maki, Y. J. Org. Chem. 1992, 57, 5268.
44. (b) Česnek, M.; Hocek, M.; Holý, A. Collect. Czech. Chem. Commun. 2000, 65, 1357.
45. Hocek, M.; Holý, A. Collect. Czech. Chem. Commun. 1995, 60, 1386.
46. (a) Sečkářová, P.; Marek, R.; Maliňáková, K.; Kolehmainen, E.; Hocková, D.; Hocek, M.; Sklenář, V. Tetrahedron Lett. 2004, 45, 6259.
47. (b) Šponer, J.; Hobza, P. Collect. Czech. Chem. Commun. 2003, 68, 2231.
48. Sutcliffe, E. Y.; Robins, R. K. J. Org. Chem. 1963, 28, 1662.
49. Oh, C.-H.; Kim, H.-K.; Lee, S.-C.; Oh, C.; Yang, B.-S.; Rhee, H. J.; Cho, J.-H. Arch. Pharm. (Weinheim) 2001, 334, 345.
50. Brown, D. J.; Jones, R. L.; Angyal, A. M.; Grigg, G. W. J. Chem. Soc., Perkin Trans. 1 1972, 1819.