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Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Three Component Coupling of Alcohol, Azide and Alkynes Using CuO Nanoparticles
Corresponding Author(s) : Buchi Reddy Reguri
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
A one-pot reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles from the alcohols via copper oxide nanoparticles (nano CuO) catalyzed nucleophilic substitution of alcohol with azide, followed by azide-alkyne 1,3-dipolar cycloaddition (click reaction) is reported. 1,4-Disubstituted 1,2,3-triazoles are obtained in good to excellent yields from a variety of readily available alcohols without the need for the preactivation and isolation of the azide intermediates.
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References
H.C. Kolb, M.G. Finn and K.B. Sharpless, Angew. Chem. Int. Ed., 40, 2004 (2001).
R. Huisgen, in ed.: A. Padwa, In 1,3-Dipolar Cycloaddition Chemistry, Wiley: New York (1984).
V.V. Rostovtsev, L.G. Green, V.V. Fokin and K.B. Sharpless, Angew. Chem., Int. Ed., 41, 2596 (2002).
H. Srinivas and K. Sudhir, J. Org. Chem., 71, 364 (2006).
E.H. Ryu and Y. Zhao, Org. Lett., 7, 1035 (2005).
P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, B. Voit, J. Pyun, J.M.J. Frechet, K.B. Sharpless and V.V. Fokin, Angew. Chem. Int. Ed., 43, 3928 (2004).
D.B. Ramachary and C.F. Barbas III, Chem. Eur. J., 10, 5323 (2004).
A. Prasad, W. Dehaen, V.V. Fokin and E.V. der Eycken, Org. Lett., 6, 4223 (2004).
S. Chittaboina, F. Xie and Q. Wang, Tetrahedron Lett., 46, 2331 (2005).
D.R. Buckle, C.J.M. Rockell, H. Smith and B.A. Spicer, J. Med. Chem., 29, 2269 (1986).
M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert and B.H. Yagi, J. Med. Chem., 43, 953 (2000).
R. Alvarez, S. Velazquez,A. San-Felix, S. Aquaro, E. De Clercq, C.F. Perno, A. Karlsson, J. Balzarini and M.J. Camarasa, J. Med. Chem., 37, 4185 (1994).
H. Wamhoff, in eds.: A.R. Katritzky and C.W. Rees, In Comprehensive Heterocyclic Chemistry, Pergamon: Oxford, Vol. 5, pp. 669-732 (1984).
E.F.V. Scriven and K. Turnbull, Chem. Rev., 88, 351 (1988).
Y. Ju, D. Kumar and R. S. Varma, J. Org. Chem., 71, 6697 (2006).