Intermolecular hydrogen abstraction reaction between nitrogen radicals in purine rings and alkyl ethers: A highly selective method for the synthesis of N-9 alkylated purine nucleoside derivatives

Advanced Synthesis and Catalysis

Volumn 353, Issue 1, 2011, Pages 53-56

  Guo, Hai Ming ^a   Xia, Chao ^a   Niu, Hong Ying ^b   Zhang, Xiao Ting ^a   Kong, Si Nan ^a   Wang, Dong Chao ^a   Qu, Gui Rong ^a  

^a HENAN NORMAL UNIVERSITY   (China)

^b HENAN INSTITUTE OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

alkyl ethers; intermolecular hydrogen abstraction reaction; nitrogen radicals; purine nucleoside derivatives

Indexed keywords

EID: 79251514990     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000682     Document Type: Article

References (44)

1. R. Garg, S. P. Gupta, H. Gao, M. S. Babu, A. K. Debnath, C. Hansch, Chem. Rev. 1999, 99, 3525
2. W. B. Parker, Chem. Rev. 2009, 109, 2880.
3. A. J. Wagstaff, D. Faulds, K. L. Goa, Drugs 1994, 47, 153
4. P. D. Welsby, J. Infect. 1994, 28, 121
5. A. D. Ruiter, R. N. Thin, Drugs 1994, 47, 297
6. E. De Clercq, Collect. Czech. Chem. Commun. 1998, 63, 480
7. S. J. Safrin, H. S. Jaffe, Adv. Exp. Med. Biol. 1999, 458, 111
8. E. De Clercq, A. Holà , I. Rosenberg, T. Sakuma, J. Balzarini, P. C. Maudgal, Science (Washington, D.C.) 1986, 323, 464
9. R. R. Webb, J. C. Martin, Tetrahedron Lett. 1987, 28, 4953
10. P. Doláková, M. DraäínskÃ, M. Masojídková, V. Åolínová, V. Kaåiäka, A. Holã, Eur. J. Med. Chem. 2009, 44, 2408
11. W. A. Bowles, F. H. Schneider, L. R. Lewis, R. K. Robins, J. Med. Chem. 1963, 6, 471.
12. H. Rosemeyer, Chem. Biodiversity 2004, 1, 361.
13. A. I. Votruba, J. Med. Chem. 2002, 45, 1918
14. U. Diederichsen, D. Weicherding, N. Diezemanna, Org. Biomol. Chem. 2005, 3, 1058
15. G. A. Sheikha, P. L. Colla, A. G. Loi, Nucleosides Nucleotides Nucleic Acids 2002, 21, 619
16. V. S. Rana, V. A. Kumarp, K. N. Ganesh, Tetrahedron 2001, 57, 1311
17. V. S. Rana, V. A. Kumar, K. N. Ganesh, Bioorg. Med. Chem. Lett. 1997, 7, 2837
18. C. Cheng, T. Shimo, K. Somekawa, M. Baba, Tetrahedron 1998, 54, 2031.
19. A. Holã, H. Dvoåáková, M. Masojí dková, J. Jindåich, J. Med. Chem. 1996, 39, 4073
20. N. F. Zakirova, A. V. Shipitsyn, E. F. Belanovb, M. V. Jasko, Bioorg. Med. Chem. Lett. 2004, 14, 3357.
21. F. Vandendriessche, R. Snoeck, G. Janssen, J. Med. Chem. 1992, 35, 1458
22. P. Franchetti, G. A. Sheikha, L. Cappellacci, J. Med. Chem. 1995, 38, 4007
23. S. Vrbková, M. DraÄ ínskà , A. Holà , Tetrahedron: Asymmetry 2007, 18, 2233.
24. M. H. Zhong, M. J. Robins, J. Org. Chem. 2006, 71, 8901.
25. C. G. Francisco, A. J. Herrera, E. Suárez, J. Org. Chem. 2002, 67, 7439
26. A. Boto, D. Hernández, R. Hernández, E. Suárez, J. Org. Chem. 2003, 68, 5310
27. C. Betancor, R. Freire, I. Pérez-Martín, T. Prangé, E. Suárez, Org. Lett. 2002, 4, 1295
28. A. Boto, D. Hernández, R. Hernández, E. Suárez, J. Org. Chem. 2006, 71, 1938
29. G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095
30. J. Robertson, J. Pillai, R. K. Lush, Chem. Soc. Rev. 2001, 30, 94
31. K. Furuta, T. Nagata, H. Yamamoto, Tetrahedron Lett. 1988, 29, 2215
32. J. C. Lopez, R. Alonso, B. F. Reid, J. Am. Chem. Soc. 1989, 111, 6471
33. S. Kim, C. J. Lim, S. E. Song, H. Y. Kang, Synlett 2001, 688.
34. C. G. Francisco, A. J. Herrera, E. Suárez, J. Org. Chem. 2003, 68, 1012
35. A. Martín, I. Pérez-Martín, E. Suárez, Org. Lett. 2005, 7, 2027
36. H. Togo, Y. Hoshina, T. Muraki, H. Nakayama, M. Yokoyama, J. Org. Chem. 1998, 63, 5193.
37. G. R. Qu, R. Xia, X. N. Yang, J. G. Li, D. C. Wang, H. M. Guo, J. Org. Chem. 2008, 73, 2416
38. H. M. Guo, P. Li, H. Y. Niu, D. C. Wang, G. R. Qu, J. Org. Chem. 2010, 75, 6016
39. H. M. Guo, Y. Y. Wu, H. Y. Niu, D. C. Wang, G. R. Qu, J. Org. Chem. 2010, 75, 3863
40. G. R. Qu, Z. J. Mao, H. Y. Niu, D. C. Wang, C. Xia, H. M. Guo, Org. Lett. 2009, 11, 1745
41. G. R. Qu, L. Zhao, D. C. Wang, J. Wu, H. M. Guo, Green Chem. 2008, 10, 287
42. G. R. Qu, J. Wu, Y. Y. Wu, F. Zhang, H. M. Guo, Green Chem. 2009, 11, 760
43. H. M. Guo, J. Wu, H. Y. Niu, D. C. Wang, F. Zhang, G. R. Qu, Bioorg. Med. Chem. Lett. 2010, 20, 3098.
44. C. G. Francisco, R. Freire, A. J. Herrera, I. Pérez-Martín, E. Suárez, Org. Lett. 2002, 4, 1959.