Controllable synthesis of bis(1,2,3-triazole)s and 5-alkynyl-triazoles via temperature effect on copper-catalyzed Huisgen cycloaddition

Tetrahedron

Volumn 69, Issue 47, 2013, Pages 9939-9946

  Li, Lingjun ^a   Fan, Xincui ^a   Zhang, Yang ^a   Zhu, Anlian ^a   Zhang, Guisheng ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

5 Alkynyl triazoles; Bis(1,2,3 triazole)s; Nucleoside analogues

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 5 ALKYNYL 1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; AZIDE; BIS(1,2,3 TRIAZOLE)DERIVATIVE; COPPER; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CLICK CHEMISTRY; CYCLOADDITION; DERIVATIZATION; OXIDATIVE COUPLING; PRIORITY JOURNAL; REACTION TIME; SOLVENT EFFECT; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 84885959828     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.09.093     Document Type: Article

References (49)

1. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
2. A.R. Bogdan, S.V. Jerome, K.N. Houk, and K. James J. Am. Chem. Soc. 134 2012 2127
3. M. Zibinsky, and V.V. Fokin Angew. Chem., Int. Ed. 52 2013 1507
4. N.D. Adhikary, and P. Chattopadhyay J. Org. Chem. 77 2012 5399
5. C.W. Tornoe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
6. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
7. M. Tischler, D. Nasu, M. Empting, S. Schmelz, D.W. Heinz, P. Rottmann, H. Kolmar, G. Buntkowsky, D. Tietze, and O. Avrutina Angew. Chem., Int. Ed. 51 2012 3708
8. J.P. MacDonald, J.J. Badillo, G.E. Arevalo, A. Silva-García, and A.K. Fran ACS Comb. Sci. 14 2012 285
9. K. Tars, D. Vullo, A. Kazaks, J. Leitans, A. Lends, A. Grandane, R. Zalubovskis, A. Scozzafava, and C.T. Supuran J. Med. Chem. 56 2013 293
10. L. Li, C.C. Siebrands, Z. Yang, L. Zhang, A.H. Guse, and L. Zhang Org. Biomol. Chem. 50 2010 1843
11. J.E. Poelma, K. Ono, D. Miyajima, T. Aida, K. Satoh, and C.J. Hawke ACS Nano 6 2012 10845
12. T. Gong, B.J. Adzima, N.H. Baker, and C.N. Bowman Adv. Mater. 25 2013 2024
13. S.E. Habnouni, V. Darcos, X. Garric, J.-P. Lavigne, B. Nottelet, and J. Coudane Adv. Funct. Mater. 21 2011 3321
14. R.J. Thibault, K. Takizawa, P. Lowenheilm, B. Helms, J.L. Mynar, J.M.J. Fréchet, and C.J. Hawker J. Am. Chem. Soc. 128 2006 12084
15. H.C. Kolb, and K.B. Sharpless Drug Discov. Today 8 2003 1128
16. W.S. Horne, C.D. Stout, and M.R. Ghadiri J. Am. Chem. Soc. 125 2003 9372
17. W.S. Horne, M.K. Yadav, C.D. Stout, and M.R. Ghadiri J. Am. Chem. Soc. 126 2004 15366
18. V.D. Bock, D. Speijer, H. Hiemstraa, and J.H. van Maarseveen Org. Biomol. Chem. 5 2007 971
19. J.M. Fernańdez-Hernańdez, J.I. Beltrań, V. Lemaur, M.-D. Gálvez-López, C.-H. Chien, F. Polo, E. Orselli, R. Fröhlich, J. Cornil, and L. De Cola Inorg. Chem. 52 2013 1812
20. C.B. Anderson, A.B.S. Elliott, C.J. McAdam, K.C. Gordon, and J.D. Crowley Organometallics 32 2013 788
21. G. Aromía, L.A. Barriosa, O. Roubeaub, and P. Gamez Coord. Chem. Rev. 255 2011 485
22. K.-C. Chang, I.-H. Su, A. Senthilvelan, and W.-S. Chun Org. Lett. 9 2007 3363
23. N.L. Kilah, M.D. Wise, C.J. Serpell, A.L. Thompson, N.G. White, K.E. Christensen, and P.D. Beer J. Am. Chem. Soc. 132 2010 11893
24. Y. Hua, and A.H. Flood Chem. Soc. Rev. 39 2010 1262
25. J.E. Hein, J.C. Tripp, L.B. Krasnova, K.B. Sharpless, and V.V. Fokin Angew. Chem., Int. Ed. 48 2009 8018
26. B.H.M. Kuijpers, G.C.T. Dijkmans, S. Groothuys, P.J.L.M. Quaedflieg, R.H. Blaauw, F.L. van Delft, and F.P.J.T. Rutjes Synlett 2005 3059
27. J.H. Huang, S.J.F. Macdonald, and J.P.A. Harrity Chem. Commun. 2009 436
28. Y.-M. Wu, J. Deng, Y. Li, and Q.-Y. Chen Synthesis 2005 1314
29. L. Li, G. Zhang, A. Zhu, and L. Zhang J. Org. Chem. 130 2008 3630
30. L. Li, R. Li, A. Zhu, G. Zhang, and L. Zhang Synlett 2011 874
31. R. Yan, K. Sander, E. Galante, V. Rajkumar, A. Badar, M. Robson, E. El-Emir, M.F. Lythgoe, R.B. Pedley, and E. Årstad J. Am. Chem. Soc. 135 2013 703
32. S. Chuprakov, N. Chernyak, A.S. Dudnik, and V. Gevorgyan Org. Lett. 9 2007 2333
33. L. Ackermann, R. Jeyachandran, H.K. Potukuchi, P. Novak, and L. Buettner Org. Lett. 12 2010 2056
34. H. Jiang, Z. Feng, A. Wang, X. Liu, and Z. Chen Eur. J. Org. Chem. 2010 1227
35. L. Ackermann, R. Vicente, and R. Born Adv. Synth. Catal. 350 2008 741
36. V.D. Bock, H. Hiemstra, and J.H. van Maarseveen Eur. J. Org. Chem. 2006 51
37. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302
38. U. Monkowius, S. Ritter, B. Konig, M. Zabel, and H. Yersin Eur. J. Inorg. Chem. 29 2007 4597
39. J.T. Fletcher, B.J. Bumgarner, N.D. Engels, and D.A. Skoglund Organometallics 27 2008 5430
40. J.D. Crowley, and P.H. Bandeen Dalton Trans. 39 2010 612
41. A. Fürstner, and V. Mamane J. Org. Chem. 67 2002 6264
42. A. Fürstner, and J.W.J. Kennedy Chem. - Eur. J. 12 2006 7398
43. Y. Angell, and K. Burgess Angew. Chem., Int. Ed. 46 2007 3649
44. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952
45. Z.-J. Zheng, F. Ye, L.-S. Zheng, K.-F. Yang, G.-Q. Lai, and L.-W. Xu Chem. - Eur. J. 18 2012 14094
46. B. Gerard, J. Ryan, A.B. Beeler, and J.A. Porco Jr. Tetrahedron 62 2006 6405
47. Triazolyl-copper complex intermediate has been previously proposed in the literature: V.O. Rodionov, S. Presolski, D.D. Díaz, V.V. Fokin, and M.G. Finn J. Am. Chem. Soc. 129 2007 12705
48. E.A. Lewis, and W.B. Tolman Chem. Rev. 104 2004 1047
49. L.M. Mirica, X. Ottenwaelder, and T.D.P. Stack Chem. Rev. 104 2004 1013