Citation: Mao Runvze, Sun Lifeng, Wang Yong-Shi, Zhou Min-Min, Xiong De-Cai, Li Qin, Ye Xin-Shan. N-9 Alkylation of purines via light-promoted and metal-free radical relay[J]. Chinese Chemical Letters, ;2018, 29(1): 61-64. doi: 10.1016/j.cclet.2017.08.005 shu

N-9 Alkylation of purines via light-promoted and metal-free radical relay

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

Corresponding author: Li Qin, liqin@bjmu.edu.cn Ye Xin-Shan, xinshan@bjmu.edu.cn

Received Date: 4 June 2017
Revised Date: 3 July 2018
Accepted Date: 14 July 2017
Available Online: 3 January 2017

Figures(4)

A metal-free and light-promoted approach to the synthesis of N-9 alkylated purine nucleoside derivatives, via a CF₃ radical triggered radical relay pathway, has been developed. Purine nucleoside derivatives were prepared regioselectively in good to high yields. Photosensitizers and metals are free in this transformation. Visible light or even sunlight can be used as the source of light for the reactions.
- Photochemistry,
- Alkylation of purines,
- Regioselectivity,
- Metal free,
- CF₃ radical
1. [1]
  (a) R. Garg, S. P. Gupta, H. Gao, et al., Chem. Rev. 99(1999) 3525-3602;
  (b) W. B. Parker, Chem. Rev. 109(2009) 2880-2893.
2. [2]
  (a) A. J. Wagstaff, D. Faulds, K. L. Goa, Drugs 47(1994) 153-205;
  (b) P. D. Welsby, J. Infect. 28(1994) 121-129;
  (c) A. D. Ruiter, R. N. Thin, Drugs 47(1994) 297-304;
  (d) W. A. Bowles, F. H. Schneider, L. R. R. Lewis, K. Robins, J. Med. Chem. 6(1963) 467-471;
  (e) R. B. Yan, Y. F. Wu, J. Liu, X. L. Zhang, X. S. Ye, Chin. Chem. Lett. 24(2013) 273-278.
3. [3]
  H. Rosemeyer, Chem. Biodivers. 1(2004) 361-401. doi: 10.1002/(ISSN)1612-1880
4. [4]
  (a) R. J. Haslam, M. M. L. Davidson, J. V. Desjardins, Biochem. J. 176(1978) 83-95;
  (b) T. A. Rich, R. C. Shepard, S. T. Mosley, J. Clin Oncol. 22(2004) 2214-2232;
  (c) J. C. Martin, M. J. M. Hitchcock, E. De Clercq, W. H. Prusoff, Antiviral Res. 85(2010) 34-38;
  (d) E. De Clercq, Rev. Med. Virol. 19(2009) 287-299.
5. [5]
  (a) A. I. Votruba, J. Med Chem. 45(2002) 1918-1929;
  (b) U. Diederichsen, D. Weicherding, N. Diezemanna, Org. Biomol. Chem. 3(2005) 1058-1066;
  (c) G. A. Sheikha, P. L. Colla, A. G. Loi, Nucleosides Nucleotides Nucleic Acids 21(2002) 619-635.
6. [6]
  N.F. Zakirova, A.V. Shipitsyn, E.F. Belanovb, M.V. Jasko, Med. Bioorg, Chem. Lett. 14(2004) 3357-3360. doi: 10.1016/j.bmcl.2003.12.107
7. [7]
  (a) F. Vandendriessche, R. Snoeck, G. Janssen, J. Med. Chem. 35(1992) 1458-1465;
  (b) P. Franchetti, G. A. Sheikha, L. Cappellacci, J. Med. Chem. 38(1995) 4007-4013.
8. [8]
  H.M. Guo, C. Xia, H.Y. Niu, et al., Adv. Synth. Catal. 353(2011) 53-56. doi: 10.1002/adsc.201000682
9. [9]
  I. Buslov, X. Hu, Adv. Synth. Catal. 356(2014) 3325-3330. doi: 10.1002/adsc.201400646
10. [10]
  R. Huang, C.S. Xie, L. Huang, J.H. Liu, Tetrahedron 69(2013) 577-582. doi: 10.1016/j.tet.2012.11.020
11. [11]
  (a) M. Ochiai, S. Yamane, M. Hoque, M. Saito, K. Miyamoto, Chem. Commun. 48(2012) 5280-5282;
  (b) L. He, J. Yu, J. Zhang, X. Q. Yu, Org. Lett. 9(2007) 2277-2280;
  (c) T. Fuchigami, T. Sato, T. Nonaka, J. Org. Chem. 51(1986) 427-432;
  (d) K. S. Feldman, M. M. Bruendl, K. Schildknegt, A. C. Bohnstedt, J. Org. Chem. 61(1996) 5440-5452;
  (e) H. Kim, J. Kim, S. Cho, S. Chang, J. Am. Chem. Soc. 133(2011) 16382-16385;
  (f) M. Ochiai, K. Miyamoto, T. Kaneaki, S. Hayashi, W. Nakanishi, Science 332(2011) 448-451;
  (g) A. P. Antonchick, R. Samanta, K. Kulikov, J. Lategahn, Angew. Chem Int. Ed. 50(2011) 8605-8608.
12. [12]
  (a) K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev. 116(2016) 10035-10074;
  (b) C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 113(2013) 5322-5363;
  (c) N. A. Romero, D. A. Nicewicz, Chem. Rev. 116(2016) 10075-10166;
  (d) D. M. Arias-Rotondo, J. K. McCusker, Chem. Soc. Rev. 45(2016) 5803-5820.
13. [13]
  T. Umemoto, Chem. Rev. 96(1996) 1757-1778. doi: 10.1021/cr941149u
14. [14]
  B.P. Roberts, Chem. Soc. Rev. 28(1999) 25-35. doi: 10.1039/a804291h
15. [15]
  Y. Yasu, T. Koike, M. Akita, Angew. Chem. Int. Ed. 51(2012) 9567-9571. doi: 10.1002/anie.v51.38
16. [16]
  (a) E. Arceo, I. D. Jurberg, A. Álvarez-Fernández, P. Melchiorre, Nat. Chem. 5(2013) 750-756;
  (b) S. Mattia, E. Arceo, I. D. Jurberg, C. Cassani, P. Melchiorre, J. Am. Chem. Soc. 137(2015) 6120-6123;
  (c) J. F. Franz, W. B. Kraus, K. Zeitler, Chem. Commun. 51(2015) 8280-8283;
  (d) M. Tobisu, T. Furukawa, N. Chatani, Chem. Lett. 42(2013) 1203-1205.
17. [17]
  X. Wang, Y. Ye, S. Zhang, et al., J. Am. Chem. Soc. 133(2011) 16410-16413. doi: 10.1021/ja207775a
18. [18]
  (a) C. P. Zhang, H. Wang, A. Klein, et al., J. Am. Chem. Soc. 135(2013) 8141-8144;
  (b) R. Z. Mao, D. C. Xiong, F. Guo, et al., Org. Chem. Front. 3(2016) 737-743.
19. [19]
  S.Z. Zard, Chem. Soc. Rev. 37(2008) 1603-1618. doi: 10.1039/b613443m
20. [20]
  Z. Cekovic, J. Serb. Chem. Soc. 70(2015) 287-318.
21. [21]
  (a) J. C. K. Chu, T. Rovis, Nature 539(2016) 272-275;
  (b) G. J. Choi, Q. L. Zhu, D. C. Miller, C. J. Gu, R. R. Knowles, Nature 539(2016) 268-271;
  (c) A. Noble, D. W. C. MacMillan, J. Am. Chem. Soc. 136(2014) 11602-11605.
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