New and practical method for synthesis of 1- and 1,3-substituted xanthines

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2237-2240

  Zavialov, Ilia A ^a   Dahanukar, Vilas H ^a   Nguyen, Hoa ^a   Orr, Cecilia ^a   Andrews, David R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

XANTHINE DERIVATIVE;

ALKALINITY; ALKYLATION; ARTICLE; DEPROTECTION REACTION; MOLECULAR MECHANICS; POLYMERIZATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKYLATION; CARBAMATES; IMIDAZOLES; XANTHINES;

EID: 3142778544     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049272n     Document Type: Article

References (22)

1. (a) Stevanovich, V. Drug News Perspect. 1989, 2, 82.
2. (b) Jacobsen, K. A.; van Galen, P. J. M.; Williams, M. J. Med. Chem. 1992, 35, 407.
3. (a) Wang, Y.; Chackalamannil, S.; Hu, Z.; Boyle, C. D.; Lankin, C M.; Xia, Y.; Xu, R.; Asberom, T.; Pissarnitski, D.; Stamford, A. W. Greenlee, W. J.; Skell, J.; Kurowski, S.; Vemulapalli, S.; Palamanda, J. Chintala, M.; Wu, P.; Myers, J.; Wang, P. Bioorg. Med. Chem. Lett. 2002 12, 3149.
4. (b) Strappaghetti, G.; Corsano, S.; Barbaro, R.; Giannaccini, G. Betti, L. Bioorg. Med. Chem. 2001, 9, 575.
5. (c) Buckle, D. R.; Arch, J. R. S.; Connolly, B. J.; Fenwick, A. E.; Foster, K. A.; Murray, K. J.; Readshaw, S. A.; Smallridge, M.; Smith, D. G. J. Med. Chem. 1994, 37, 476.
6. (d) Peet, N. P.; Lentz, N. L.; Meng, E. C.; Dudley, M. W.; Ogden, A. M. L.; Demeter, D. A.; Weintraub, H. J. R.; Bey, P. J. Med. Chem. 1990, 33, 3127.
7. (a) Lister, J. H. The Purines, Supplement 1. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Weissberger, A., Eds.; John Wiley: New York, 1996; Vol. 54.
8. (b) Traube, W. Ber. Deut. Chem. Ges. 1900, 33, 3035.
9. (a) Weyler, S.; Hayallah, A. M.; Muller, C. E. Tetrahedron 2003, 59, 47.
10. (b) Muller, C. E.; Sandoval-Ramirez, J. Synthesis 1995, 1295.
11. (c) Muller, C. E. Synthesis 1993, 125.
12. (d) Vishnyakova, T. P.; Golubeva, I. A.; Glebova, E. V. Russ. Chem. Rev. 1985, 54, 249.
13. (e) Hutzenlaub, W.; Pfleiderer, W. Liebigs Ann. Chem. 1979, 1847.
14. (a) Herr, R. J.; Vogt, P. F.; Meckler, H.; Trova, M. P. J. Org. Chem. 2002, 67, 188.
15. (b) Bridson, P. K.; Wang, X. Synthesis 1995, 7, 855.
16. (c) Hergueta, A. R.; Figuera, M. J.; Lopez, C.; Caamano, O.; Fernandez, F.; Rodriguez-Borges, J. E. Chem. Pharm. Bull. 2002, 50, 1379.
17. Itaya, T.; Ogawa, K. Tetrahedron. Lett. 1978, 32, 2907.
18. See Supporting Information for detailed experimental procedures.
19. (a) Singh, S. B. Tetrahedron Lett. 1995, 36, 12, 2009.
20. (b) Nohara, F.; Nishii, M.; Ogawa, K.; Isono, K.; Ubukata, M.; Fujii, T.; Itaya, T.; Saito, T. Tetrahedron Lett. 1987, 28, 12, 1287.
21. (c) Forbes, I. T.; Johnson, C. N.; Thompson, M. J. Chem. Soc. Perkin Trans, 1 1992, 275.
22. Izawa, K.; Shiragami, H.; Yamashita, K. U.S. Patent 6 087 497, 2000.