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RSC Advances
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ARTICLE
Green Chemistry
Table 5 Comparison among efficiency of PVA@Cu(II) Schiff base
complex with the reported catalysts in the literature for preparation
of 5-phenyl 1H-tetrazole
DOI: 10.1039/C6RA19631D
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Solvent/ T
Yield
(%)
Catalyst
Time (h)
Ref.
(C)
Cu(OAC)2 (15.0 mol%)
DMF/ 120
DMF/ 140
12
96
90
21
Cu-MCM-41 (0.05
mol%)
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12
22
35
Bi(OTf)3
DMF/120
H2O/ R. T.
24
87
98
PVA@Cu(II) Schiff base
complex
a
0.12
-
a Present work
Because in contrast to the reported catalysts in the literature, which
catalyze the preparation of 5-substituted-1H-tetrazoles in DMF as a
toxic solvent, long reaction times, under high temperatures (>100
oC), PVA@Cu(II) Schiff base complex works in water as a green
solvent, very short reaction times and at room temperature. The
other notable advantages of this catalyst are: a) its preparation in
water, and b) its stability and reusability, so it can be reused five
runs without significant reactivity loss.
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8 B. Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah and R.Narender,
Synlett., 2010, 3, 391.
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Hrabálek, Synthesis, 2009, 13, 2175.
10 H. Yoneyama, Y. Usami, S. Komeda and S. Harusawa, Synthesis,
2013, 45, 1051.
11 D. Cantillo, B. Gutmann and C. O. Kappe, J. Org. Chem. Soc.,
2012, 77, 10882.
12 D. Cantillo, B. Gutmann and C. O. Kappe, J. Am. Chem. Soc.,
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Conclusion
We have reported preparation of novel heterogeneous recoverable
and reusable polyvinyl alcohol immobilized Cu(II) Schiff base
complex in water from simple and available reagents, which is able
to catalyze green formation of 5-substituted 1H-tetrazoles from
aldehydes, hydroxylamine hydrochloride and sodium azide at room
temperature in short reaction times in water. The catalyst was
characterized with FT-IR, UV-Vis, 1H NMR, TGA and ICP instruments.
Simplicity, high efficiency and cost effectiveness, easy work-up of
the catalyst and the products are among the other notable
advantages of this protocol. Various aliphatic and aromatic
aldehydes served as suitable substrates for the preparation of
substituted tetrazoles with high to excellent yields at room
temperature.
Acknowledgements
The authors are grateful to Research Council of Shiraz
University for the financial support of this work
16 A. Coca, E. Turek and L. Feinn, Synthetic Comm., 2015, 45, 218.
17 H. M. Najundaswamy and H. Abrahamse, Heterocycles, 2014,
89, 2137.
.
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6 | J. Name., 2012, 00, 1-3
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