Novel synthesis of difluoromethyl-containing 1,4-disubstituted 1,2,3-triazoles via a click-multicomponent reaction and desulfanylation strategy

Advanced Synthesis and Catalysis

Volumn 353, Issue 4, 2011, Pages 580-584

  Zhang, Jian ^a   Wu, Jingjing ^a   Shen, Li ^a   Jin, Guanyi ^a   Cao, Song ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Azides; Click chemistry; Desulfanylation; Difluoromethyl group; Multicomponent reactions

Indexed keywords

EID: 79952548064     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000791     Document Type: Article

References (52)

1. a) M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Barbachyn, D. E. Emmert, J. Med. Chem. 2000, 43, 953-970;
2. b) R. Alvarez, S. Velázquez, A. San-Félix, S. Aquaro, M. J. Camarasa, J. Med. Chem. 1994, 37, 4185-4194;
3. c) A. C. Cunha, J. M. Figueiredo, J. L. M. Tributino, Bioorg. Med. Chem. 2003, 11, 2051-2059;
4. d) V. D. Bock, R. Perciaccante, T. P. Jansen, H. Hiemstra, J. H. van Maarseveen, Org. Lett. 2006, 8, 919-922;
5. e) A. Dondoni, Chem. Asian J. 2007, 2, 700-708.
6. a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075;
7. Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
8. b) V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68;
9. c) L. D. Pachón, J. H. van Maarseveen, G. Rothenberg, Adv. Synth. Catal. 2005, 347, 811-815;
10. d) F. Alonso, Y. Moglie, G. Radivoy, M. Yus, Eur. J. Org. Chem. 2010, 1875-1884.
11. a) J.-P. Zhu, H. Bienaymé, Multicomponent reactions, Wiley-VCH, Weinheim, 2005;
12. b) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344;
13. Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
14. c) L.-Z. Gong, X.-H. Chen, X.-Y. Xu, Chem. Eur. J. 2007, 13, 8920-8926;
15. d) A. Dömling, Chem. Rev. 2006, 106, 17-89;
16. e) J.-J. Wu, S. Cao, Curr. Org. Chem. 2009, 13, 1791-1804;
17. f) L. Shen, S. Cao, J.-J. Wu, H. Li, J. Zhang, M.-X. Wu, X.-H. Qian, Tetrahedron Lett. 2010, 51, 4866-4869;
18. g) L. Shen, J. Zhang, S. Cao, J.-L. Yu, N.-J. Liu, J.-J. Wu, X.-H. Qian, Synlett 2008, 3058-3062;
19. h) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628-1661;
20. Angew. Chem. Int. Ed. 2005, 44, 1602-1634.
21. a) V. Malnuit, M. Duca, A. Manout, K. Bougrin, R. Benhida, Synlett 2009, 2123-2128;
22. b) M. N. S. Rad, S. Behrouzb, A. K. Nezhad, Tetrahedron Lett. 2007, 48, 3445-3449;
23. c) B. Khanetskyy, D. Dallinger, C. O. Kappe, J. Comb. Chem. 2004, 6, 884-892;
24. d) S.-L. Cui, J. Wang, Y.-G. Wang, Org. Lett. 2008, 10, 1267-1269.
25. a) P. Appukkuttan, W. Dehaen, V. V. Fokin, E. V. der Eycken, Org. Lett. 2004, 6, 4223-4225;
26. b) D. Kumour, G. Patel, V. B. Reddy, Synlett 2009, 399-402.
27. a) A. Kumar, P. S. Pandey, Org. Lett. 2008, 10, 165-168;
28. b) G. K. S. Prakash, J.-B. Hu, Y. Wang, G. A. Olah, Eur. J. Org. Chem. 2005, 2218-2223.
29. a) B. J. Elisabeth, M. M. M. Woodhead, Patent WO 2007096576, 2007;
30. b) L. David, D. Robert, S. Dean, A. Alexander, Patent WO 2007111904, 2007.
31. a) R. Sasson, A. Hagooly, S. Rozen, Org. Lett. 2003, 5, 769-771;
32. b) W. J. Middleton, J. Org. Chem. 1975, 40, 574-578;
33. c) G. A. Olah, M. Nojima, I. Kerekes, J. Am. Chem. Soc. 1974, 96, 925-927;
34. d) A. Jończyk, E. Nawrot, M. Kisielewski, J. Fluorine Chem. 2005, 126, 1587-1591;
35. e) P. Bannwarth, A. Valleix, D. Grée, R. Grée, J. Org. Chem. 2009, 74, 4646-4649.
36. a) E. Nawrot, A. Jończyk, J. Fluorine Chem. 2009, 130, 466-469;
37. b) G. K. S. Prakash, C. Weber, S. Chacko, G. A. Olah, J. Comb. Chem. 2007, 9, 920-923;
38. c) J.-B. Hu, J. Fluorine Chem. 2009, 130, 1130-1139;
39. d) R. Bastin, H. Albadri, A. C. Gaumont, M. Gulea, Org. Lett. 2006, 8, 1033-1036;
40. e) J. Zheng, Y. Li, L.-J. Zhang, J.-B. Hu, G. J. Meuzelaar, H.-J. Federsel, Chem. Commun. 2007, 5149-5151;
41. f) W. Zhang, F. Wang, J.-B. Hu, Org. Lett. 2009, 11, 2109-2112.
42. J.-J. Wu, S. Cao, N.-J. Liu, L. Shen, J.-L. Yu, J. Zhang, H. Li, X.-H. Qian, Org. Biomol. Chem. 2010, 8, 2386-2391.
43. a) A. K. Feldman, B. Colasson, V. V. Fokin, Org. Lett. 2004, 6, 3897-3899;
44. b) J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1302-1315.
45. a) Z.-Y. Yan, Y.-B. Zhao, M.-J. Fan, W.-M. Liu, Y.-M. Liang, Tetrahedron 2005, 61, 9331-9337;
46. b) I. Bae, H. Han, S. Chang, J. Am. Chem. Soc. 2005, 127, 2038-2039.
47. H. Eto, Y. Kaneko, S. Takeda, M. Tokizawa, S. Sato, Chem. Pharm. Bull. 2001, 49, 173-182.
48. J.-J. Wu, J.-H. Cheng, J. Zhang, H. Li, M.-X. Wu, L. Shen, X.-H. Qian, S. Cao, Tetrahedron 2011, 67, 285-288.
49. G. K. S. Prakash, J.-B. Hu, Acc. Chem. Res. 2007, 40, 921-930.
50. M. Pohmakotr, D. Panichakul, P. Tuchinda, V. Reutrakul, Tetrahedron 2007, 63, 9429-9436.
51. S.-Q. Zang, J. Han, T. C. W. Mak, Organometallics 2009, 28, 2677-2683.
52. E. M. Beccalli, E. Borsini, G. Broggini, G. Palmisano, S. Sottocornola, J. Org. Chem. 2008, 73, 4746-4749.