Nucleosides as reagents in multicomponent reactions: One-pot synthesis of heterocyclic nucleoside analogues incorporating pyrimidine-fused rings

Tetrahedron Letters

Volumn 54, Issue 3, 2013, Pages 220-222

  Khalafi Nezhad, Ali ^a   Divar, Masoumeh ^a   Panahi, Farhad ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Heterocyclic nucleoside analogues; Multicomponent reactions; Nucleosides; Pyrimidine

Indexed keywords

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; ACICLOVIR; ALDEHYDE; BARBITURIC ACID; FAMCICLOVIR; FUSED HETEROCYCLIC RINGS; GANCICLOVIR; NUCLEOSIDE ANALOG; NUCLEOSIDE DERIVATIVE; PENCICLOVIR; PENTOSTATIN; PHOSPHOTUNGSTIC ACID; PYRIMIDINE; REAGENT; THIOBARBITURIC ACID; VALACICLOVIR;

ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; ONE POT SYNTHESIS;

EID: 84871186295     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.11.003     Document Type: Article

References (49)

1. G. Romeo, U. Chiacchio, A. Corsaro, and P. Merino Chem. Rev. 110 2010 3337
2. P. Li, Z.A. Sergueeva, M. Dobrikov, and B.R. Shaw Chem. Rev. 107 2007 4746
3. J. Lu, N.-S. Li, S.C. Koo, and J.A. Piccirilli J. Org. Chem. 74 2009 8021
4. M. Prashad, D. Har, L. Chen, H.-Y. Kim, O. Repic, and T.J. Blacklock J. Org. Chem. 67 2002 6612
5. C.S. Stauffer, P. Bhaket, A.W. Fothergill, M.G. Rinaldi, and A. Datta J. Org. Chem. 72 2007 9991
6. M.A. Boudreau, and J.C. Vederas Org. Biomol. Chem. 5 2007 627
7. N. Kifli, T.T. Htar, E.D. Clercq, J. Balzarini, and C. Simons Bioorg. Med. Chem. 12 2004 3247
8. S. Dalencon, R.A. Youcef, M. Pipelier, V. Maisonneuve, D. Dubreuil, F. Huet, and S. Legoupy J. Org. Chem. 76 2011 8059
9. A. Okamoto, K. Tainaka, and Y. Fujiwara J. Org. Chem. 71 2006 3592
10. M.J. Sofia, W. Chang, P.A. Furman, R.T. Mosley, and B.S. Ross J. Med. Chem. 55 2012 2481
11. R.A. Tromp, R.F. Spanjersberg, J.K.F.D. Künzel, and A.P. Ijzerman J. Med. Chem. 48 2005 321
12. T. Semeraro, A. Lossani, M. Botta, C. Ghiron, R. Alvarez, F. Manetti, C. Mugnaini, S. Valensin, F. Focher, and F. Corelli J. Med. Chem. 49 2006 6037
13. B. Golankiewicz, T. Ostrowski, T. Goslinski, P. Januszczyk, J. Zeidler, D. Baranowski, and E.D. Clercq J. Med. Chem. 44 2001 4284
14. L. Colla, E.D. Clercq, R. Busson, and H. Vanderhaeghe J. Med. Chem. 26 1983 602
15. S. Tolle-Sander, K.A. Lentz, D.Y. Maeda, A. Coop, and J.E. Polli Mol. Pharm. 1 2004 40
16. C. Prasse, M. Wagner, R. Schulz, and T.A. Ternes Environ. Sci. Technol. 45 2011 2761
17. H.H. Balfour Jr., K.M. Hokanson, R.M. Schacherer, C.M. Fietzer, D.O. Schmeling, C.J. Holman, H.E. Vezina, and R.C. Brundage J. Clin. Virol. 39 2007 16
18. R. Cirelli, K. Herne, M. McCrary, P. Lee, and S.K. Tyring Antiviral Res. 29 1996 141
19. D.C. Baker, and S.R. Putt J. Am. Chem. Soc. 101 1979 6127
20. J. Stambasky, V. Kapras, M. Stefko, O. Kysilka, M. Hocek, A.V. Malkov, and P. Kocovsky J. Org. Chem. 76 2011 7781
21. R. Flores, A. Rustullet, R. Alibes, A. Alvarez-Larena, P.D. March, M. Figueredo, and J. Font J. Org. Chem. 76 2011 5369
22. J.M. Swarbrick, and B.V.L. Potter J. Org. Chem. 77 2012 4191
23. J. Cao, and X. Huang J. Comb. Chem. 10 2008 526
24. L. Feliu, P. Vera-Luque, F. Albericio, and M. Álvarez J. Comb. Chem. 9 2007 521
25. A. Dömling, W. Wang, and K. Wang Chem. Rev. 112 2012 3083
26. J. Yu, F. Shi, and L.-Z. Gong Acc. Chem. Res. 44 2011 1156
27. O.N. Burchak, L. Mugherli, M. Ostuni, J.J. Lacapere, and M.Y. Balakirev J. Am. Chem. Soc. 133 2011 10058
28. I. Monfardini, J.-W. Huang, B. Beck, J.F. Cellitti, M. Pellecchia, and A. Domling J. Med. Chem. 54 2011 890
29. H. Tomoda, and T. Doi Acc. Chem. Res. 41 2008 32
30. J.P. McDevitt, and P.T.J. Lansbury J. Am. Chem. Soc. 118 1996 3818
31. J. Cao, and X. Huang J. Comb. Chem. 10 2008 526
32. B.B. Braunheim, R.W. Miles, V.L. Schramm, and S.D. Schwartz Biochemistry 38 1999 16076
33. E.A. Taylor, K. Clinch, P.M. Kelly, L. Li, G.B. Evans, P.C. Tyler, and V.L. Schramm J. Am. Chem. Soc. 129 2007 6984
34. S.G. Modha, J.C. Trivedi, V.P. Mehta, D.S. Ermolatev, and E.V.V.D. Eycken J. Org. Chem. 76 2011 846
35. A.K. Ghosh, and J. Kass Chem. Commun. 46 2010 1218
36. X. Zhang, X. Li, X. Fan, X. Wang, D. Li, G. Qu, and J. Wang Mol. Divers. 13 2009 57
37. X. Fan, X. Zhang, L. Zhou, K.A. Keith, M.N. Pritchard, E.R. Kern, and P.F. Torrence J. Med. Chem. 49 2006 4052
38. X. Zhang, D. Li, X. Fan, X. Wang, X. Li, G. Qu, and J. Wang Mol. Divers. 14 2010 159
39. A. Khalafi-Nezhad, M.N. Soltani Rad, A.A. Moosavi-Movahedi, and M. Kosari Helv. Chim. Acta 90 2007 730
40. M.N. Soltani Rad, A. Khalafi-Nezhad, and S. Behrouz Helv. Chim. Acta 92 2009 1760
41. A. Khalafi-Nezhad, A. Zare, M.N. Soltani Rad, B. Mokhtari, and A. Parhami Synthesis 2005 419
42. A. Khalafi-Nezhad, M.N. Soltani Rad, and A. Khoshnood Synthesis 2004 583
43. M.N. Soltani Rad, A. Khalafi-Nezhad, S. Behrouz, M.A. Faghihi, A. Zare, and A. Parhami Tetrahedron 64 2008 1778
44. A. Khalafi-Nezhad, M.N. Soltani Rad, G.H. Hakimelahi, and B. Mokhtari Tetrahedron 58 2002 10341
45. A. Khalafi-Nezhad, and F. Panahi Synthesis 2011 984
46. A. Khalafi-Nezhad, S.M. Haghighi, A. Purkhosrow, and F. Panahi Synlett 2012 920
47. A. Khalafi-Nezhad, S. Sarikhani, E.S. Shahidzadeh, and F. Panahi Green Chem. 14 2012 2876
48. M.N. Soltani Rad, A. Khalafi-Nezhad, M. Divar, and S. Behrouz Phosphorus, Sulfur Silicon Relat. Elem. 2010 1943 185
49. A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, and G.R. Nejabat Can. J. Chem. 84 2006 979