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Simple Protocol for the Knoevenagel Condensation Under Solvent Free Conditions using Tungstophosphoric Acid as Catalyst
Corresponding Author(s) : Abdulrahman I. Alharthi
Asian Journal of Chemistry,
Vol. 31 No. 10 (2019): Vol 31 Issue 10
Abstract
The effect of calcination on the performance of tungstophosphoric acid for the product of Knoevenagel condensation was investigated. Substituted aldehydes and dimedone has been used in the presence of calcined tungstophosphoric acid as a heterogeneous catalyst using grinding method at room temperature. The results of reactions revealed that calcined tungstophosphoric acid has superior catalytic activity comparing to non-calcined catalyst in terms of yield and reaction time. Maximum yield of model compound was achieved by using 10 mol% of calcined catalyst in a reaction time that does not exceed 10 min, whereas the yield at same amount of non-calcined catalyst was 86 % in a reaction time of 35 min.
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- Y. Ogiwara, K. Takahashi, T. Kitazawa and N. Sakai, J. Org. Chem., 80, 3101 (2015); https://doi.org/10.1021/acs.joc.5b00011.
- M.L. Deb and P.J. Bhuyan, Tetrahedron Lett., 46, 6453 (2005); https://doi.org/10.1016/j.tetlet.2005.07.111.
- G. Jenner, Tetrahedron Lett., 42, 243 (2001); https://doi.org/10.1016/S0040-4039(00)01930-4.
- D. Prajapati, K.C. Lekhok, J.S. Sandhu and A.C. Ghosh, J. Chem. Soc. Perkin Trans. I, 959 (1996); https://doi.org/10.1039/P19960000959.
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- S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); https://doi.org/10.1016/j.molcata.2006.12.039.
- A.V. Narsaiah and K. Nagaiah, Synth. Commun., 33, 3825 (2003); https://doi.org/10.1081/SCC-120025194.
- W. Lehnert, Tetrahedron Lett., 11, 4723 (1970); https://doi.org/10.1016/S0040-4039(00)89377-6.
- G. Bartoli, M. Bosco, A. Carlone, R. Dalpozzo, P. Galzerano, P. Melchiorre and L. Sambri, Tetrahedron Lett., 49, 2555 (2008); https://doi.org/10.1016/j.tetlet.2008.02.093.
- L.F. Tietze and U. Beifuss, In Comprehensive Organic Synthesis, Pergamon: New York, vol. 2, pp 341-394 (1991).
- I.V. Kozhevnikov, Chem. Rev., 98, 171 (1998); https://doi.org/10.1021/cr960400y.
- M. Misono, Catal. Rev., Sci. Eng., 30, 339 (1988); https://doi.org/10.1080/01614948808078622.
- J.K. Rajput and G. Kaur, Tetrahedron Lett., 53, 646 (2012); https://doi.org/10.1016/j.tetlet.2011.11.109.
- K. Nowiñska, R. Fiedorow and J. Adamiec, J. Chem. Soc. Faraday Trans., 87, 749 (1991); https://doi.org/10.1039/FT9918700749.
- T. Okuhara, T. Nishimura, H. Watanabe and M. Misono, J. Mol. Catal., 74, 247 (1992); https://doi.org/10.1016/0304-5102(92)80242-9.
- W. Klemperer and W. Shum, J. Am. Chem. Soc., 99, 3544 (1977); https://doi.org/10.1021/ja00452a080.
- I.V. Kozhevnikov, J. Mol. Catal. A, 262, 86 (2007); https://doi.org/10.1016/j.molcata.2006.08.072.
References
Y. Ogiwara, K. Takahashi, T. Kitazawa and N. Sakai, J. Org. Chem., 80, 3101 (2015); https://doi.org/10.1021/acs.joc.5b00011.
M.L. Deb and P.J. Bhuyan, Tetrahedron Lett., 46, 6453 (2005); https://doi.org/10.1016/j.tetlet.2005.07.111.
G. Jenner, Tetrahedron Lett., 42, 243 (2001); https://doi.org/10.1016/S0040-4039(00)01930-4.
D. Prajapati, K.C. Lekhok, J.S. Sandhu and A.C. Ghosh, J. Chem. Soc. Perkin Trans. I, 959 (1996); https://doi.org/10.1039/P19960000959.
G. Bartoli, R. Beleggia, S. Giuli, A. Giuliani, E. Marcantoni, M. Massaccesi and M. Paoletti, Tetrahedron Lett., 47, 6501 (2006); https://doi.org/10.1016/j.tetlet.2006.07.031.
S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); https://doi.org/10.1016/j.molcata.2006.12.039.
A.V. Narsaiah and K. Nagaiah, Synth. Commun., 33, 3825 (2003); https://doi.org/10.1081/SCC-120025194.
W. Lehnert, Tetrahedron Lett., 11, 4723 (1970); https://doi.org/10.1016/S0040-4039(00)89377-6.
G. Bartoli, M. Bosco, A. Carlone, R. Dalpozzo, P. Galzerano, P. Melchiorre and L. Sambri, Tetrahedron Lett., 49, 2555 (2008); https://doi.org/10.1016/j.tetlet.2008.02.093.
L.F. Tietze and U. Beifuss, In Comprehensive Organic Synthesis, Pergamon: New York, vol. 2, pp 341-394 (1991).
I.V. Kozhevnikov, Chem. Rev., 98, 171 (1998); https://doi.org/10.1021/cr960400y.
M. Misono, Catal. Rev., Sci. Eng., 30, 339 (1988); https://doi.org/10.1080/01614948808078622.
J.K. Rajput and G. Kaur, Tetrahedron Lett., 53, 646 (2012); https://doi.org/10.1016/j.tetlet.2011.11.109.
K. Nowiñska, R. Fiedorow and J. Adamiec, J. Chem. Soc. Faraday Trans., 87, 749 (1991); https://doi.org/10.1039/FT9918700749.
T. Okuhara, T. Nishimura, H. Watanabe and M. Misono, J. Mol. Catal., 74, 247 (1992); https://doi.org/10.1016/0304-5102(92)80242-9.
W. Klemperer and W. Shum, J. Am. Chem. Soc., 99, 3544 (1977); https://doi.org/10.1021/ja00452a080.
I.V. Kozhevnikov, J. Mol. Catal. A, 262, 86 (2007); https://doi.org/10.1016/j.molcata.2006.08.072.