Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF 3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 614-618

  Rozin, Yury A ^a   Leban, Johann ^b   Dehaen, Wim ^c   Nenajdenko, Valentine G ^d   Muzalevskiy, Vasiliy M ^d   Eltsov, Oleg S ^a   Bakulev, Vasiliy A ^a  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b 4SC AG   (Germany)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

1 Trifluoromethyl 1,3 dicarbonyl compounds; 4 Acyl 5 trifluoromethyl 1,2,3 triazoles; 3+2 Cycloaddition; Azides

Indexed keywords

1 TRIFLUOROMETHYL 1,3 DICARBONYL; 1,2 DICARBONYL DERIVATIVE; 4 ACYL 5 TRIFLUOROMETHYL 1,2,3 TRIAZOLE; AZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 82955167872     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.110     Document Type: Article

References (50)

1. D. Kumar, V.B. Reddy, A. Kumar, D. Mandal, R. Tiwari, and K. Parang Bioorg. Med. Chem. Lett. 21 2011 449 452
2. E.N. Silva Jr., B.C. Cavalcanti, T.T. Guimaraes, M.C.F.R. Pinto, I.O. Cabral, C. Pessoa, L.V. Costa-Lotufo, M.O. de Moraes, C.K.Z. de Andrade, M.R. dos Santos, C.A. de Simone, M.O.F. Goulart, and A.V. Pinto Eur. J. Med. Chem. 46 2011 399 410
3. I. Pibiri, and S. Buscemi Curr. Bioact. Compd. 6 2010 208 242
4. X.-L. Wang, K. Wan, and C.H. Zhou Eur. J. Med. Chem. 45 2010 4631 4639
5. S.-J. Yan, Y.-J. Liu, Y.-L. Chen, L. Liu, and J. Lin Bioorg. Med. Chem. Lett. 20 2010 5225 5228
6. K. Slamova, P. Marhol, K. Bezouska, L. Lindkvist, S. Hansen, V. Kren, and H.H. Jensen Bioorg. Med. Chem. Lett. 20 2010 4263 4265
7. C.G. Oliva, N. Jagerovic, P. Goya, I. Alkorta, J. Elguero, R. Cuberes, and A. Dordal ARKIVOC 2 2010 127 147
8. L. Ackermann, and H.P. Kumar Org. Biomol. Chem. 8 2010 4503 4513
9. A. Tam, U. Arnold, B. Matthew, M.B. Soellner, and R.T. Raines J. Am. Chem. Soc. 129 2007 12670 12671
10. J.M. Holub, and K. Kirshenbaum Chem. Soc. Rev. 39 2010 1325 1337
11. A. Brik, J. Muldoon, Y.-C. Lin, J.H. Elder, D.S. Goodsell, A.J. Olson, V.V. Fokin, K.B. Sharpless, and C.-H. Wong ChemBioChem 4 2003 1246 1248
12. M.J. Soltis, H.J. Yeh, K.A. Cole, N. Whittaker, R.P. Wersto, and E.C. Kohn Drug Metab. Dispos. 24 1996 799 806
13. R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, C.-F.N. Perno, A. Karlsson, J. Balzarini, and M.J. Camarasa J. Med. Chem. 37 1994 4185 4194
14. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
15. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
16. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302 1315
17. N.V. Sokolova, G.V. Latyshev, N.V. Lukashev, and V.G. Nenajdenko Org. Biomol. Chem. 9 2011 4921 4926
18. V.G. Nenajdenko, A.V. Gulevich, N.V. Sokolova, A.V. Mironov, and E.S. Balenkova Eur. J. Org. Chem. 2010 1445 1449
19. V.P. Krivopalov, and O.P. Shkurko Russ. Chem. Rev. 74 2005 339 379
20. N.T. Pokhodylo, V.S. Matiychuk, and M.D. Obushak Synth. Commun. 40 2010 1932 1938
21. F. Stazi, D. Cancogni, L. Turco, P. Westerduin, and S. Bacchi Tetrahedron Lett. 51 2010 5385 5387
22. V.R. Kamalraj, S. Senthil, and P. Kannan J. Mol. Struct. 892 2008 210 215
23. I.A. Ol'shevskaya, M.Y. Kornilov, and M.N. Smirnov Chem. Heterocycl. Compd. 8 1990 938 940
24. L.V. Batog, V.Y. Rozhkov, and M.I. Strukova Mendeleev Commun. 12 2002 159 161
25. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004 Wiley-VCH Weinheim 320
26. C. Jäckel, and B. Koksch Eur. J. Org. Chem. 2005 4483 4503
27. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
28. J.-P. Bégué, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 John Wiley New York, NY
29. K.L. Kirk Curr. Top. Med. Chem. 6 2006 1447 1456
30. K.L. Kirk Org. Process Res. Dev. 13 2008 305 321
31. F.M.D. Ismail J. Fluorine Chem. 118 2002 27 33
32. F.M.D. Ismail, M.G.B. Drew, and M.J. Dascombe Chem. Today 27 2009 16 20
33. J.A. Gladysz, D.P. Curran, and I.T. Horváth Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim
34. D. O'Hagan Chem. Soc. Rev. 37 2008 308 319
35. A. Gakh, and K.L. Kirk Fluorinated Heterocycles 2008 Oxford University
36. V.A. Petrov Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications 2009 John Wiley
37. V.G. Nenajdenko, A.V. Sanin, and E.S. Balenkova Molecules 2 1997 186 232
38. V.G. Nenajdenko, A.V. Sanin, and E.S. Balenkova Russ. Chem. Rev. 1999 483 505
39. S.V. Druzhinin, E.S. Balenkova, and V.G. Nenajdenko Tetrahedron 63 2007 7753 7808
40. V.M. Muzalevskiy, A.V. Shastin, E.S. Balenkova, G. Haufe, and V.G. Nenajdenko Synthesis 23 2010 3905 3929
41. O. Serdyuk, A. Butin, and V. Abaev J. Fluorine Chem. 131 2010 296 319
42. O. Serdyuk, A. Butin, V. Abaev, and V.G. Nenajdenko Synthesis 2011 2505 2529
43. V.G. Nenajdenko, and E.S. Balenkova ARKIVOC i 2011 246 328
44. L.J.T. Danence, Y. Gao, M. Li, Y. Huang, and J. Wang Chem. - Eur. J. 17 2011 3584 3587
45. V.Y. Sosnovskikh, and B.I. Usachev Mendeleev Commun. 2002 75 76
46. S. Diezi, D. Ferri, A. Vargas, T. Mallat, and A. Baiker J. Am. Chem. Soc. 128 2006 4048 4057
47. J.C. Sloop, C.L. Bumgardner, G. Washington, W.D. Loehle, S.S. Sankar, and A.B. Lewis J. Fluorine Chem. 127 2006 780 786
48. W.V.F. Fabian, V.A. Bakulev, and C.O. Kappe J. Org. Chem. 63 1998 5801 5805
49. S.P. Singh, and D. Kumar J. Chem. Res., Synop. 1997 142 143
50. R.R. Kale, V. Prasad, H.A. Hussain, and V.K. Tiwari Tetrahedron Lett. 51 2010 5740 5743