Copper-catalyzed huisgen 1,3-dipolar cycloaddition under oxidative conditions: Polymer-assisted assembly of 4-acyl-1-substituted-1,2,3-triazoles

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6540-6549

  Diz, Paula M ^a,b   Coelho, Alberto ^a,b   El Maatougui, Abdelaziz ^a,b   Azuaje, Jhonny ^a,b   Caamaño, Olga ^b   Gil, Álvaro ^b   Sotelo, Eddy ^a,b  

^a s n   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIPOLAR CYCLOADDITIONS; COPPER-CATALYZED HUISGEN 1 ,3-DIPOLAR CYCLOADDITION; HOMOGENEOUS CONDITIONS; OXIDATIVE CONDITIONS; POLYMER-ASSISTED; POLYMER-SUPPORTED REAGENTS; THERMODYNAMIC INSTABILITY;

COPPER; CYCLOADDITION; POLYMERS; POLYSTYRENES;

CATALYSIS;

1,2,3 TRIAZOLE DERIVATIVE; COPPER; POLYSTYRENE 1,5,7 TRIAZABICYCLO[4,4,0]DECENE; POLYSTYRENE 2 IODOXYBENZAMIDE; POLYSTYRENE DERIVATIVE; UNCLASSIFIED DRUG; ALKYNE; AZIDE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; HUISGEN REACTION; OXIDATION; THERMODYNAMICS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYSTYRENES; THERMODYNAMICS; TRIAZOLES;

EID: 84880028545     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400800j     Document Type: Article

References (66)

1. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302
2. Medal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952
3. Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457
4. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
5. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128
6. Sharpless, K. B.; Manetsch, R. Expert Opin. Drug Discovery 2006, 1, 525
7. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278
8. Nandivada, H.; Jiang, X. W.; Lahann, J. Adv. Mater. 2007, 19, 2197
9. Fournier, D.; Hoogenboom, R.; Schubert, U. Chem. Soc. Rev. 2007, 36, 1369
10. Yan, R.; Sander, K.; Galante, E.; Rajkumar, V.; Badar, A.; Robson, M.; El-Emir, E.; Lythgoe, M. F.; Pedley, R. B.; Arstad, E. J. Am. Chem. Soc. 2013, 135, 703
11. Ke, C.; Smaldone, R. A.; Kikuchi, T.; Li, H.; Davis, A. P.; Stoddart, J. F. Angew. Chem., Int. Ed. 2013, 52, 381
12. Budin, I.; Devaraj, N. K. J. Am. Chem. Soc. 2012, 134, 751
13. Tornøe, C. W.; Christensen, C.; Medal, M. J. Org. Chem. 2002, 67, 3057
14. Rostovtset, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
15. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853
16. Rodionov, V. O.; Presolski, S. I.; Diaz, D. D.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12705
17. Tanaka, K.; Kageyama, C.; Fukase, K. Tetrahedron Lett. 2007, 48, 6475
18. Xu, W. M.; Huang, X.; Tang, E. J. Comb. Chem. 2005, 7, 726
19. Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638
20. Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. J. Med. Chem. 2005, 48, 499
21. Rodionov, V. O.; Presolski, S. I.; Gardinier, S.; Lim, Y. H.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12696
22. Girard, C.; Onen, E.; Aufort, M.; Beauviére, S.; Samson, E.; Herscovici, J. Org. Lett. 2006, 8, 1689
23. Smith, C. D.; Baxendale, I. R.; Lanners, S.; Hayward, J. J.; Smith, S. C.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 1559
24. Sirion, U.; Bae, Y. J.; Lee, B. S.; Chi, D. Y. Synlett 2008, 2326
25. Chan, T. R.; Fokin, V. V. QSAR Comb. Sci. 2007, 26, 1274
26. Ozkal, E.; Özçubukçu, S.; Jimeno, C.; Pericàs, M. A. Catal. Sci. Technol. 2012, 2, 195
27. Caliendo, G.; Fiorino, F.; Perissutti, E.; Severino, B.; Scolaro, D.; Gessi, S.; Cattabriga, E.; Borea, P. A.; Santagada, V. Eur. J. Pharm. Sci. 2002, 16, 15
28. Calderone, V.; Giorgi, I.; Livi, O.; Martinotti, E.; Mantuano, E.; Martelli, A.; Nardi, A. Eur. J. Med. Chem. 2005, 40, 521
29. Blass, B. E.; Coburn, K.; Lee, W.; Fairweather, N.; Fluxe, A.; Wu, S.; Janusz, J. M.; Murawsky, M.; Fadayel, G. M.; Fang, B.; Hare, M.; Ridgeway, J.; White, R.; Jackson, C.; Djandjighian, L.; Hedges, R.; Wireko, F. C.; Ritter, A. L. Bioorg. Med. Chem. Lett. 2006, 16, 4629
30. Pardin, C.; Roy, I.; Lubell, W. D.; Keillor, J. W. Chem. Biol. Drug Des. 2008, 72, 189
31. Cohen, B. J.; Kraus, M. A.; Patchornik, A. J. Am. Chem. Soc. 1981, 103, 7620
32. Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Polymer-Assisted Solution-Phase Methods for Chemical Library Synthesis. In Solid-Phase Organic Synthesis; Burgess, K., Ed.; John Wiley: New York, 2000; pp 149-194.
33. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815
34. Chassaing, S.; Kumarraja, M.; Souna-Sido, A. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883
35. Miao, T.; Wang, L. Synthesis 2008, 363
36. Park, I. S.; Kwon, M. S.; Kim, Y.; Lee, J. S.; Park, J. Org. Lett. 2008, 10, 497
37. Kantam, M. L.; Jaya, V. S.; Sreedhar, B.; Rao, M. M.; Choudary, B. M. J. Mol. Catal. A: Chem. 2006, 256, 273
38. Sharghi, H.; Khalifeh, R.; Doroodmand, M. M. Adv. Synth. Catal. 2009, 351, 207
39. Lipshutz, B. H.; Taft, B. R. Angew. Chem., Int. Ed. 2006, 45, 8235
40. Angell, Y.; Burgess, K. Angew Chem., Int. Ed. 2007, 46, 3649
41. Coelho, A.; Diz, P.; Caamaño, O.; Sotelo, E. Adv. Synth. Catal. 2010, 352, 1179
42. Chung, W. J.; Ki, D. K.; Lee, Y. S. Tetrahedron Lett. 2003, 44, 9251
43. Barontini, M.; Bernini, R.; Crisante, F.; Fabrizi, G. Tetrahedron 2010, 66, 6047
44. Satam, V.; Harad, A.; Rajule, R.; Pati, H. Tetrahedron 2010, 66, 7659
45. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537
46. Zhdankin, V. V.; Koposov, A. Y.; Netzel, B. C.; Yashin, N. V.; Ferguson, M. J.; Rempel, B. P.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 2194
47. Lecarpentier, P.; Crosignani, S.; Linclau, B. Mol. Diversity 2005, 9, 341
48. Jang, H. S.; Chung, W. J.; Lee, Y.-S. Tetrahedron Lett. 2007, 48, 3731
49. Bastide, J.; Henri-Rousseau, O. Cycloadditons and Cyclizations Involving Triple Bonds. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Interscience Publishers: London, 1978; pp 447-522.
50. Huisgen, R. 1,3-Dipolar Cycloadditions-Introduction, Survey, Mechanism. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; pp 1-176.
51. Palacios, F.; Renata, A. M.; Pagalday, J. Heterocycles 1994, 38, 95
52. Katritzky, A. R.; Zhang, Y.; Singh, S. K.; Steel, P. J. ARKIVOC 2003, xv, 47
53. Kacprzack, K. Synlett 2005, 943
54. Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897
55. Yadav, J. S.; Reddy, B. V. S.; Reddy, G. M.; Chary, D. N. Tetrahedron Lett. 2007, 48, 8773
56. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223
57. Moorthy, J. N.; Singhal, N.; Senapati, K. Tetrahedron Lett. 2006, 47, 1757
58. Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686
59. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301
60. Gaab, M.; Bellemin-Laponnaz, S.; Gade, L. H. Chem.-Eur. J. 2009, 15, 5450
61. Houghten, R. A. Proc. Natl. Acad. Sci. 1985, 82, 5131
62. Buzas, A.; Gagosz, F. J. Am. Chem. Soc. U.S.A. 2006, 128, 12614
63. Hwang, S.; Bae, H.; Kim, S.; Kim, S. Tetrahedron 2012, 68, 1460
64. Chassaing, S.; Kumarraja, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883
65. Cuevas, F.; Oliva, A. I.; Pericas, M. A. Synlett 2010, 1873
66. Roque, D. R.; Neill, J. L.; Antoon, J. W.; Stevens, E. P. Synthesis 2005, 15, 2497