Regioselective and One-Pot Synthesis of 1,2,3-Triazoles and β-Hydroxytriazoles
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Table 6 Comparison of the results of SiO2/CuSO4 with
CuSO4•5H2O
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Dosage of
Entry
Catalyst
Yield Time
88% 30 h
Ref.
catalyst
CuSO4•5H2O 1 mol%
CuSO4•5H2O 16 mg
[19]
3a
5a
3a
5a
92%
85%
75%
4 h
3 h
6 h
[17]
10 mg
This work
This work
SiO2/CuSO4
10 mg
SiO2/CuSO4
This results show that amount, time and recyclability
of SiO2/CuSO4 in these reactions is good. For this rea-
son, we believe that this is one of the fastest and better
catalyst system procedures for synthesis of 1,2,3-tri-
azoles and β-hydroxytriazoles in good yields.
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Petersen, J. L.; Berteina-Raboin, S.; Nolan, S. P.; Agrofolio, L. A.
Synthesis 2008, 141.
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2004, 6, 2853; (b) Gerard, B.; Ryan, J.; Beeler, A. B.; Porco, J. A. J.
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Conclusions
In conclusion, we have introduced a catalytic system
based on SiO2/CuSO4, can catalyze the 1,3-dipolar
cycloaddition of azides and terminal alkynes. The
SiO2/CuSO4 is quickly prepared from commercially
available reagents under mild conditions. We believe
that the herein described methodology fulfils the re-
quirements of a true click reaction, namely: (a) wide
scope, (b) simple reaction conditions, (c) readily avail-
able starting materials and reagents, (d) easily removed
solvent and (e) simple removal of by-products and prod-
uct isolation. In view of the results presented above, we
also believe that this is one of the fastest procedures
ever reported for the title reaction, but involving milder
conditions and without the inherent limitations and at
ambient temperature in good yields. Further research to
extend the substrate scope and on the reaction mecha-
nism is underway and will be reported in due course.
The operational simplicity of this method makes it at-
tractive for preparative applications as well as for the
synthesis of screening libraries for drug discovery.
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Li, N.; Zhao, M.; Shi, W.; Maa, C.; Chen, B. Green Chem. 2010, 12,
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2009, 11, 4680.
Acknowledgement
We gratefully acknowledge financial support from
the Research Council of Islamic Azad University of
Karaj.
[17] Yadav, J. S.; Reddy, B. V. S.; Reddy, G. M.; Chary, D. N.
Tetrahedron Lett. 2007, 48, 8773.
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