Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides

Synlett

Volumn , Issue 6, 2005, Pages 943-946

  Kacprzak, Karol ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

1,2,3 Triazoles; 1,3 Dipolar cycloadditon; Click chemistry; One pot synthesis

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; AZIDE; BENZYL DERIVATIVE; HALIDE;

ARTICLE; CORROSION; DECOMPOSITION; DRUG ISOLATION; FILTRATION; LABELING INDEX; MOLECULAR RECOGNITION; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 17144419614     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864809     Document Type: Article

References (20)

1. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Heterocycles 2003, 60, 1225; and references cited therein.
2. (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
3. (b) Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003, 8, 1128.
4. (a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 1053.
5. (b) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, Ch.-H. J. Am. Chem. Soc. 2003, 125, 9588.
6. (c) Brik, A.; Muldoon, J.; Lin, Y.-Ch.; Elder, J. H.; Goodsell, D. S.; Olson, A. J.; Fokin, V. V.; Sharpless, K. B.; Wong, Ch.-H. ChemBioChem 2003, 4, 1246.
7. (d) Link, A. J.; Tirrell, D. J. Am. Chem. Soc. 2003, 125, 11164.
8. (e) Deiteres, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. Ch.; Schultz, P. G. J. Am. Chem. Soc. 2003,125, 11782.
9. (f) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
10. (g) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686.
11. (h) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609.
12. Maksikova, A. V.; Serebryakova, E. S.; Tikhonova, L. G.; Vereshagin, L. I. Chem. Heterocycl. Compd. 1980, 1284.
13. Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897.
14. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223.
15. Blass, B. E.; Coburn, K. R.; Faulkner, A. L.; Seible, W. L.; Srivastava, A. Tetrahedron Lett. 2003, 44, 2153.
16. (a) Grundmann, C. In Houben-Weyl, Methoden der organischen Chemie, 4th Ed., Vol. 10/3; Muller, E., Ed.; Thieme: Stuttgart, 1965, 777.
17. (b) See also references in Ref. 7
18. Alvarez, S. G.; Alvarez, M. T. Synthesis 1997, 413.
19. Cu(I) formed under this condition is a catalyst for highly regioslective 1,4-triazole formation see: Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
20. Progress of the reaction can be monitored by TLC.