Azoles as suzuki cross-coupling leaving groups: Syntheses of 6-arylpurine 2′-deoxynucleosides and nucleosides from 6-(lmidazol-1-yl)- and 6-(1,2,4-triazol-4-yl)purine derivatives

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3421-3423

  Liu, Jiangqiong ^a   Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; SUBSTITUTION REACTION; SUZUKI REACTION;

AZOLES; CATALYSIS; DEOXYRIBONUCLEOSIDES; IMIDAZOLES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PURINE NUCLEOSIDES; TRIAZOLES;

EID: 4644281584     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048490d     Document Type: Article

References (25)

1. Nucleic Acid Related Compounds. 124. Paper 123: Liu, J.; Janeba, Z.; Robins, M. J. Org. Lett. 2004, 6, 2917-2919.
2. (a) Brathe, A.; Gunderesen, L.-L.; Rise, F.; Eriksen A. B.; Vollsnes, A. V.; Wang, L. Tetrahedron 1999, 55, 211-228.
3. (b) Perez, O. D.; Chang Y.-T.; Rosania, G.; Sutherlin, D.; Schultz, P. G. Chem. Biol. 2002, 9, 475-483.
4. (a) Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. J. Med. Chem. 2000, 43, 1817-1825.
5. (b) Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. Collect. Czech. Chem. Commun. 2000, 65, 1683-1697.
6. (c) Hocke, M.; Holy, A.; Votruba, I.; Dvorakova, H. Collect. Czech. Chem. Commun. 2001, 66, 483-499.
7. Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479-1482.
8. (a) Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2601-2607.
9. (b) Nair, V.; Richardson, S. G. Synthesis 1982, 670-672.
10. (c) Francom, P.; Janeba, Z.; Shibuya, S.; Robins, M. J. J. Org. Chem. 2002, 67, 6788-6796.
11. (d) Janeba, Z.; Francom, P.; Robins, M. J. J. Org. Chem. 2003, 68, 989-992 and references therein.
12. Lin, X.; Robins, M. J. Org. Lett. 2000, 2, 3497-3499.
13. Yamashita, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 5344-5345.
14. (a) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024-8030.
15. (b) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447-3452.
16. (c) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340-1341.
17. (d) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058-3059.
18. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
19. (b) Grasa, G. A.; Viciu, M. S.; Huang, J. Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866-2873.
20. (c) Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317-3319.
21. (d) Ma, Y.; Song, C.; Jiang, W.; Xue, G.; Cannon, J. F.; Wang, X.; Andrus, M. B. Org. Lett. 2003, 5, 4635-4638.
22. (e) Altenhoff. G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690-3693.
23. Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046-6047.
24. (a) Samano, V.; Miles, R. W.; Robins, M. J. J. Am. Chem. Soc. 1994, 116, 9331-9332.
25. (b) Miles, R. W.; Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1995, 117, 5951-5957.