Multicomponent click synthesis of potentially biologically active triazoles catalysed by copper nanoparticles on activated carbon in water

Heterocycles

Volumn 84, Issue 2, 2012, Pages 1033-1044

  Alonso, Francisco ^a   Moglie, Yanina ^a   Radivoy, Gabriel ^b   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856512336     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)81     Document Type: Article

References (59)

1. For recent reviews, see for instance: A. Pace and P. Pierro, Org. Biomol. Chem., 2009, 7, 4337 (oxadiazoles)
2. M. S. Kedar, N. S. Dighe, S. R. Pattan, D. S. Musmade, D. Thakur, M. Bhosale, and V. M. Gaware, Pharma Chemica, 2010, 2, 249 (benzimidazoles)
3. G. Palmisano, A. Penoni, M. Sisti, F. Tibiletti, S. Tollari, and K. M. Nicholas, Curr. Org. Chem., 2010, 14, 2409 (indoles)
4. R. Mishra and I. Tomar, Int. J. Pharm. Sci. Res., 2011, 2, 758 (pyrimidines)
5. A. Schmidt and A. Dreger, Curr. Org. Chem., 2011, 15, 1423 (pyrazoles).
6. For recent reviews, see for instance: C. Nájera and J. M. Sansano, Org. Biomol. Chem., 2009, 7, 4567
7. P. P. Gadhave, N. S. Dighe, S. R. Pattan, P. Deotarse, D. S. Musmade, and R. V. Shete, Ann. Biol. Res., 2010, 1, 82
8. I. Pibiri and S. Buscemi, Curr. Bioact. Comp., 2010, 6, 208.
9. For a review, see: H. C. Kolb, M. G. Finn, and K. B. Sharpless, Angew. Chem. Int. Ed., 2001, 40, 2004.
10. For recent reviews and monographs, see: A. D. Moorhouse and J. E. Moses, ChemMedChem, 2008, 3, 715
11. J.-F. Lutz and Z. Zarafshani, Adv. Drug Delivery Rev., 2008, 60, 958; Click Chemistry for Biotechnology and Materials Science,' ed. by J. Lahann, John Wiley & Sons, Hoboken, 2009
12. Applications of click chemistry themed issue', ed. by M. G. Finn and V. Fokin, Chem. Soc. Rev., 2010, 39, issue n 4.
13. R. Huisgen, G. Szeimies, and L. Moebius, Chem. Ber., 1965, 98, 4014
14. R. Huisgen, Pure Appl. Chem., 1989, 61, 613.
15. C. W. Tornøe, C. Christensen, and M. Meldal, J. Org. Chem., 2002, 67, 3057.
16. V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596.
17. For reviews, see: V. D. Bock, H. Hiemstra, and J. H. van Maarseveen, Eur. J. Org. Chem., 2006, 51
18. M. Meldal and C. W. Tornøe, Chem. Rev., 2008, 108, 2952
19. P. Appukkuttan and E. Van der Eycken, Eur. J. Org. Chem., 2008, 1133
20. C. O. Kappe and E. Van der Eycken, Chem. Soc. Rev., 2010, 39, 1280
21. M. G. Finn and V. V. Fokin, 'Catalysis Without Precious Metals,' ed. by R. Morris Bullock, Wiley-VCH, Weinheim, 2010, pp. 235-260.
22. For reviews, see: F. Alonso, G. Radivoy, and M. Yus, Russ. Chem. Bull., Int. Ed., 2003, 52, 2563
23. F. Alonso and M. Yus, Chem. Soc. Rev., 2004, 33, 284
24. F. Alonso and M. Yus, Pure Appl. Chem., 2008, 80, 1005
25. F. Alonso, P. Riente, and M. Yus, Acc. Chem. Res., 2011, 44, 379.
26. F. Alonso, C. Vitale, G. Radivoy, and M. Yus, Synthesis, 2003, 443
27. F. Alonso, Y. Moglie, G. Radivoy, C. Vitale, and M. Yus, Appl. Catal. A: Gen., 2004, 271, 171
28. G. Radivoy, F. Alonso, Y. Moglie, C. Vitale, and M. Yus, Tetrahedron, 2005, 61, 3859.
29. F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, Tetrahedron Lett., 2009, 50, 2358
30. F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, Eur. J. Org. Chem. 2010, 1875.
31. For a recent contribution, see: F. Alonso, T. Melkonian, Y. Moglie, and M. Yus, Eur. J. Org. Chem., 2011, 2524.
32. For recent reviews on the multicomponent synthesis of heterocycles, see: B. A. Arndtsen, Chem. Eur. J., 2009, 15, 302
33. I. Akritopoulou-Zanze and S. W. Djuric, Top. Heterocycl. Chem., 2010, 25, 231
34. B. Jiang, T. Rajale, W. Wever, S.-J. Tu, and G. Li, Chem. Asian J., 2010, 5, 2318.
35. F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, Adv. Synth. Catal., 2010, 352, 3208
36. F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, Org. Biomol. Chem., 2011, 9, 6385
37. F. Alonso, Y. Moglie, G. Radivoy, and M. Yus, J. Org. Chem., in press, doi: org/10.1021/jo2016339.
38. I. A. Khan and E. A. Abourashed, 'Leung's Encyclopedia of Common Natural Ingredients', 3rd edn., John Wiley & Sons, Hoboken, 2010, pp. 443-448.
39. A. Slominski, Am. J. Physiol. Cell Physiol., 2008, 295, C293.
40. 'The Merck Index', 13th edn., Merck & Co., Inc., Whitehouse Station, NJ, USA, 2001, p. 5353.
41. For reviews, see: Y. L. Angell and K. Burgess, Chem. Soc. Rev., 2007, 36, 1674
42. K. A. Kalesh, H. Shi, J. Ge, and S. Q. Yao, Org. Biomol. Chem., 2010, 8, 1749.
43. For a review, see: W. J. Malaisse, Int. J. Mol. Med., 1998, 2, 383.
44. For reviews, see: S. Dedola, S. A. Nepododiev, and R. A. Field, Org. Biomol. Chem., 2007, 5, 1006
45. A. Dondoni, Chem. Asian J., 2007, 2, 700
46. A. Dondoni, Org. Biomol. Chem., 2010, 8, 3366
47. V. Aragão-Leoneti, V. L. Campo, A. S. Gomes, R. A. Field, and I. Carvalho, Tetrahedron, 2010, 66, 9475.
48. E. van Dijkum, R. Danac, D. J. Hughes, R. Wood, A. Rees, B. L. Wilkinson, and A. J. Fairbanks, Org. Biomol. Chem., 2009, 7, 1097.
49. R. Kumar, P. R. Maulik, and A. K. Misra, Glycoconj. J., 2008, 25, 595.
50. 'The Merck Index', 13th edn., Merck & Co., Inc., Whitehouse Station, NJ, USA, 2001, p. 3746.
51. J. Matthews, 'Endogenous Toxins: Targets for Disease Treatment and Prevention,' Vol. 1, ed. by P. O'Brien and R. W. Bruce, Wiley-VCH, Weinheim, 2010, pp. 227-248.
52. 'The Merck Index', 13th edn., Merck & Co., Inc., Whitehouse Station, NJ, USA, 2001, p. 2223.
53. For a recent, review, see: G. Saher, S. Quintes, and K.-A. Nave, Neuroscientist, 2011, 17, 79.
54. O. Kaczmarek, H. A. Scheidt, A. Bunge, D. Föse, S. Karsten, A. Arbuzova, D. Huster, and J. Liebscher, Eur. J. Org. Chem., 2010, 1579.
55. For a review on antipyretic therapy including phenacetin, see: R. Botting, Front. Biosci., 2004, 9, 956.
56. 'Ninth Report on Carcinogens,' PB2000-107509, 2000, pp. III-4, III-180.
57. W. F. J. Hogendorf, C. P. Verhagen, E. Malta, N. Goosen, H. S. Overkleeft, D. V. Filippov, and G. A. Van der Marel, Tetrahedron, 2009, 65, 10430.
58. Z. Hakki, B. Cao, A. M. Heskes, J. Q. D. Goodger, I. E. Woodrow, and S. J. Williams, Carbohydr. Res., 2010, 345, 2079.
59. M. Ohkubo, S. Mochizuki, T. Sano, Y. Kawaguchi, and S. Okamoto, Org. Lett., 2007, 9, 773.