A straightforward synthesis of benzofuran- and indole-substituted 1,2,3-triazoles via click chemistry

Synthesis

Volumn , Issue 22, 2009, Pages 3853-3859

  Fiandanese, Vito ^a   Bottalico, Daniela ^a   Marchese, Giuseppe ^a   Punzi, Angela ^a   Quarta, Maria Rosaria ^a   Fittipaldi, Marianna ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Azides; Benzofurans; Cycloadditions; Indoles; Triazoles

Indexed keywords

BENZOFURANS; CLICK CHEMISTRY; CYCLOADDITIONS; INDOLE DERIVATIVES;

NITROGEN COMPOUNDS;

1,2,3 TRIAZOLE DERIVATIVE; 2 (1 BENZYL 1H 1,2,3 TRIAZOLE 4 YL) 1H INDOLE; 2 (1 OCTYL 1H 1,2,3 TRIAZOL 4 YL) 1H INDOLE; 2 [(1 BENZYL 1H 1,2,3 TRIAZOLE 4 YL)ETHYNYL] 1H INDOLE; 2 [1 (2 PHENYLETHYL) 1H 1,2,3 TRIAZOLE 4 YL] 1H INDOLE; 2 [1 (4 IODOBENZYL) 1H 1,2,3 TRIAZOLE 4 YL] 1H INDOLE; 2 [1 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOLE 4 YL] 1H INDOLE; 2 [[1 (2 PHENYLETHYL) 1H 1,2,3 TRIAZOL 4 YL]ETHYNYL] 1H INDOLE; 4 (BENZOFURAN 2 YL) 1 (2 IODOBENZYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 (2 PHENYLETHYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 (3 IODOBENZYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 (4 IODOBENZYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 BENZYL 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YL) 1 OCTYL 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YLETHYNYL) 1 (2 PHENYLETHYL) 1H 1,2,3 TRIAZOLE; 4 (BENZOFURAN 2 YLETHYNYL) 1 BENZYL 1H 1,2,3 TRIAZOLE; ALKYNE; BENZOFURAN DERIVATIVE; COPPER DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DRUG SYNTHESIS; ROOM TEMPERATURE;

EID: 73949096692     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217017     Document Type: Article

References (45)

1. (a) Morales-Sanfrutos, J.; Ortega-Munoz, M.; Lopez-Jaramillo, J.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. J. Org. Chem. 2008, 73, 7768.
2. (b) Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018.
3. (c) Such, G. K.; Quinn, J. F.; Quinn, A.; Tjipto, E.; Caruso, F. J. Am. Chem. Soc. 2006, 128, 9318.
4. (d) Ryu, E.-H.; Zhao, Y. Org. Lett. 2005, 7, 1035.
5. (e) Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753.
6. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
7. (a) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1986, 29, 2269.
8. (b) Buckle, D. R.; Outred, D. J.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1983, 26, 251.
9. Giffin, M. J.; Heaslet, H.; Brik, A.; Lin, Y.-C.; Cauvi, G.; Wong, C.-H.; McRee, D. E.; Elder, J. H.; Stout, C. D.; Torbett, B. E. J. Med. Chem. 2008, 51, 6263.
10. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
11. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
12. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
13. (a) Jurícek, M.; Kouwer, P. H. J.; Rehák, J.; Sly, J.; Rowan, A. E. J. Org. Chem. 2009, 74, 21.
14. (b) Broggi, J.; Díez-González, S.; Petersen, J. L.; Berteina-Raboin, S.; Nolan, S. P.; Agrofoglio, L. A. Synthesis 2008, 141.
15. (c) Li, P.; Wang, L.; Zhang, Y. Tetrahedron 2008, 64, 10825.
16. (d) Jlalia, I.; Elamari, H.; Meganem, F.; Herscovici, J.; Girard, C. Tetrahedron Lett. 2008, 49, 6756.
17. (e) Wang, Z.-X.; Zhao, Z.-G. J. Heterocycl. Chem 2007, 44, 89.
18. (f) Chassaing, S.; Kumarraja, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883.
19. (g) Yoo, E. J.; Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.; Sharpless, K. B.; Chang, S. Angew. Chem. Int. Ed. 2007, 46, 1730.
20. (h) Bertrand, P.; Gesson, J. P. J. Org. Chem. 2007, 72, 3596.
21. (i) Luu, T.; McDonald, R.; Tykwinski, R. R. Org. Lett. 2006, 8, 6035.
22. (j) Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem. Eur. J. 2006, 12, 7558.
23. (k) Lipshutz, B. H.; Taft, B. R. Angew. Chem. Int. Ed. 2006, 45, 8235.
24. (l) Reddy, K. R.; Rajgopal, K.; Kantam, M. L. Synlett 2006, 957.
25. Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron Lett. 2003, 44, 9087.
26. (a) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2004, 60, 11421.
27. (b) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. J. Organomet. Chem. 2005, 690, 3004.
28. (c) Fiandanese, V.; Bottalico, D.; Cardellicchio, C.; Marchese, G.; Punzi, A. Tetrahedron 2005, 61, 4551.
29. (d) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2006, 62, 5126.
30. For a comprehensive review, see: Fiandanese, V.; Bottalico, D. Curr. Org. Chem. 2009, 13, 554.
31. Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 53.
32. Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 7301.
33. Ito, H.; Arimoto, K.; Sensui, H.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977.
34. (a) Vitérisi, A.; Orsini, A.; Weibel, J.-M.; Pale, P. Tetrahedron Lett. 2006, 47, 2779.
35. (b) Létinois-Halbes, U.; Pale, P.; Berger, S. J. Org. Chem. 2005, 70, 9185.
36. (c) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039.
37. (d) Bertus, P.; Halbes, U.; Pale, P. Eur. J. Org. Chem. 2001, 4391.
38. Yamamoto, Y. Chem. Rev. 2008, 108, 3199.
39. (a) Shin, K.; Ogasawara, K. Synlett 1995, 859.
40. (b) Marshall, J. A.; Yu, B. J. Org. Chem. 1994, 59, 324.
41. Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1993, 58, 3435.
42. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1992, 33, 4905.
43. Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 7048.
44. Pérez-Serrano, L.; Casarrubios, L.; Domínguez, G.; González-Pérez, P.; Pérez-Castells, J. Synthesis 2002, 1810.
45. Bergman, J.; Venemalm, L. J. Org. Chem. 1992, 57, 2495.