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This work is licensed under a Creative Commons Attribution 4.0 International License.
Ammonium Chloride: An Efficient and Environmentally benign Catalyst for Knoevenagel Condensation of Carbonyl and Active Methylene Compounds
Corresponding Author(s) : S. Tasqeeruddin
Asian Journal of Chemistry,
Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020
Abstract
In the present study, a rapid, simple and an efficient procedure for the Knoevenagel condensation of various carbonyl and active methylene compounds in ethanol at a moderate temperature in the presence of a catalytic amount of an efficient, environmentally benign and inexpensive ammonium chloride is reported. Simple reaction procedure, economic and ecofriendly catalyst, mild reaction conditions and good to excellent yield of the products are the characteristic features of this study. The non-extractive workup/purification, economic and environmentally benign catalyst make this operationally straightforward procedure affordable for large scale.
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- L.F. Tietze and P. Saling, Synlett, 1992, 281 (1992); https://doi.org/10.1055/s-1992-21339
- I. Kim, S.G. Kim, J. Choi and G.H. Lee, Tetrahedron, 64, 664 (2008); https://doi.org/10.1016/j.tet.2007.11.036
- L.F. Tietze, Chem. Rev., 96, 115 (1996); https://doi.org/10.1021/cr950027e
- D. Basavaiah, A.J. Rao and T. Satyanarayana, Chem. Rev., 103, 811 (2003); https://doi.org/10.1021/cr010043d
- D.E. Sammelson and M.J. Kurth, Chem. Rev., 101, 137 (2001); https://doi.org/10.1021/cr000086e
- R.R. Huddleston and M.J. Krische, Synlett, 12 (2003); https://doi.org/10.1055/s-2003-36213
- S.E. Gibson and A. Stevenazzi, Angew. Chem. Int. Ed., 42, 1800 (2003); https://doi.org/10.1002/anie.200200547
- M. Moreno-Mañas and R. Pleixats, Acc. Chem. Res., 36, 638 (2003); https://doi.org/10.1021/ar020267y
- E.A. Shirokava, G.M. Segal and I.V. Torgov, Bioorg. Khim., 14, 236 (1988).
- D. Davidson and S.A. Bernhard, J. Am. Chem. Soc., 70, 3426 (1948); https://doi.org/10.1021/ja01190a060
- E.J. Corey, J. Am. Chem. Soc., 74, 5897 (1952); https://doi.org/10.1021/ja01143a021
- P. Schuster, O.E. Polansky and F. Wessely, Monatsh. Chem., 95, 53 (1964); https://doi.org/10.1007/BF00909251
- G.A. Kraus and M.E. Krolski, J. Org. Chem., 51, 3347 (1986); https://doi.org/10.1021/jo00367a017
- B.C. Ranu and R. Jana, Eur. J. Org. Chem., 3767 (2006); https://doi.org/10.1002/ejoc.200600335
- Z.J. Ren, W.G. Cao, W.Q. Tong and X.P. Jing, Synth. Commun., 32, 1947 (2002); https://doi.org/10.1081/SCC-120004844
- T.I. Reddy and R.S. Varma, Tetrahedron Lett., 38, 1721 (1997); https://doi.org/10.1016/S0040-4039(97)00180-9
- S. Shah and B. Singh, Bioorg. Med. Chem. Lett., 22, 5388 (2012); https://doi.org/10.1016/j.bmcl.2012.07.049
- W. Lehnert, Tetrahedron, 30, 301 (1974); https://doi.org/10.1016/S0040-4020(01)91461-9
- B. Green, R.I. Crane, I.S. Khaidem, R.S. Leighton, S.S. Newaz and T.E. Smyser, J. Org. Chem., 50, 640 (1985); https://doi.org/10.1021/jo00205a016
- P.S. Rao and R.V. Venkataratnam, Tetrahedron Lett., 32, 5821 (1991); https://doi.org/10.1016/S0040-4039(00)93564-0
- 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.K. Chakraborti, L. Sharma, R. Gulhane and Shivani, Tetrahedron, 59, 7661 (2003); https://doi.org/10.1016/j.tet.2003.08.007
- G. Bartoli, L. Sambri, M. Bosco, M. Locatelli, E. Marcantoni and P. Melchiorre, Synlett, 239 (2004); https://doi.org/10.1055/s-2003-44974
- G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi and L. Sambri, Eur. J. Org. Chem., 4611 (2003); https://doi.org/10.1002/ejoc.200300458
- G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, P. Melchiorre and L. Sambri, Org. Lett., 7, 427 (2005); https://doi.org/10.1021/ol047704o
- G. Bartoli, M. Locatelli, P. Melchiorre and L. Sambri, Eur. J. Org. Chem., 2037 (2007); https://doi.org/10.1002/ejoc.200600852
- M. Lakshmi Kantam, B.M. Choudary, C.V. Reddy, K. Koteswara Rao, M. Lakshmi Kantam, B.M. Choudary, K. Koteswara Rao and F. Figueras, Chem. Commun., 1033 (1998); https://doi.org/10.1039/a707874i
- J.R. Long, Chem. Health Saf., 9, 12 (2002); https://doi.org/10.1016/S1074-9098(02)00294-0
- A.M. El-Awad, R.M. Gabr and M.M. Girgis, Thermochim. Acta, 184, 205 (1991); https://doi.org/10.1016/0040-6031(91)80024-D
- S. Ghosh, J. Das and S. Chattopadhyay, Tetrahedron Lett., 52, 2869 (2011); https://doi.org/10.1016/j.tetlet.2011.03.123
- A. Zicmanis and L. Anteina, Tetrahedron Lett., 55, 2027 (2014); https://doi.org/10.1016/j.tetlet.2014.02.035
- 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
- M.L. Deb and P.J. Bhuyan, Tetrahedron Lett., 46, 6453 (2005); https://doi.org/10.1016/j.tetlet.2005.07.111
- H. Xu, L. Pan, X. Fang, B. Liu, W. Zhang, M. Lu, Y. Xu, T. Ding and H. Chang, Tetrahedron Lett., 58, 2360 (2017); https://doi.org/10.1016/j.tetlet.2017.05.006
- F. Bigi, L. Chesini, R. Maggi and G. Sartori, J. Org. Chem., 64, 1033 (1999); https://doi.org/10.1021/jo981794r
- J. Azizian, F. Teimouri and M.R. Mohammadizadeh, Catal. Commun., 8, 1117 (2007); https://doi.org/10.1016/j.catcom.2006.06.002
- T. Pirali, G.C. Tron, G. Masson and J. Zhu, Org. Lett., 9, 5275 (2007); https://doi.org/10.1021/ol7024372
- P. Janvier, X. Sun, H. Bienayme and J. Zhu, J. Am. Chem. Soc., 124, 2560 (2002); https://doi.org/10.1021/ja017563a
- D. Bonne, M. Dekhane and J. Zhu, Org. Lett., 6, 4771 (2004); https://doi.org/10.1021/ol0479388
- G.W. Wang and C.S. Jia, Lett. Org. Chem., 3, 289 (2006); https://doi.org/10.2174/157017806776114568
- H. Fang, Z. Ji-Ming, Y. Zhi-Jun and Z. Jian-Hua, Shandong Kexue, 23, 6 (2010).
- M. Hosseini-Sarvari, Can. J. Chem., 87, 1122 (2009); https://doi.org/10.1139/V09-069
- S. Genovese, F. Epifano, M.C. Marcotullio, C. Pelucchini and M. Curini, Tetrahedron Lett., 52, 3474 (2011); https://doi.org/10.1016/j.tetlet.2011.04.109
References
L.F. Tietze and P. Saling, Synlett, 1992, 281 (1992); https://doi.org/10.1055/s-1992-21339
I. Kim, S.G. Kim, J. Choi and G.H. Lee, Tetrahedron, 64, 664 (2008); https://doi.org/10.1016/j.tet.2007.11.036
L.F. Tietze, Chem. Rev., 96, 115 (1996); https://doi.org/10.1021/cr950027e
D. Basavaiah, A.J. Rao and T. Satyanarayana, Chem. Rev., 103, 811 (2003); https://doi.org/10.1021/cr010043d
D.E. Sammelson and M.J. Kurth, Chem. Rev., 101, 137 (2001); https://doi.org/10.1021/cr000086e
R.R. Huddleston and M.J. Krische, Synlett, 12 (2003); https://doi.org/10.1055/s-2003-36213
S.E. Gibson and A. Stevenazzi, Angew. Chem. Int. Ed., 42, 1800 (2003); https://doi.org/10.1002/anie.200200547
M. Moreno-Mañas and R. Pleixats, Acc. Chem. Res., 36, 638 (2003); https://doi.org/10.1021/ar020267y
E.A. Shirokava, G.M. Segal and I.V. Torgov, Bioorg. Khim., 14, 236 (1988).
D. Davidson and S.A. Bernhard, J. Am. Chem. Soc., 70, 3426 (1948); https://doi.org/10.1021/ja01190a060
E.J. Corey, J. Am. Chem. Soc., 74, 5897 (1952); https://doi.org/10.1021/ja01143a021
P. Schuster, O.E. Polansky and F. Wessely, Monatsh. Chem., 95, 53 (1964); https://doi.org/10.1007/BF00909251
G.A. Kraus and M.E. Krolski, J. Org. Chem., 51, 3347 (1986); https://doi.org/10.1021/jo00367a017
B.C. Ranu and R. Jana, Eur. J. Org. Chem., 3767 (2006); https://doi.org/10.1002/ejoc.200600335
Z.J. Ren, W.G. Cao, W.Q. Tong and X.P. Jing, Synth. Commun., 32, 1947 (2002); https://doi.org/10.1081/SCC-120004844
T.I. Reddy and R.S. Varma, Tetrahedron Lett., 38, 1721 (1997); https://doi.org/10.1016/S0040-4039(97)00180-9
S. Shah and B. Singh, Bioorg. Med. Chem. Lett., 22, 5388 (2012); https://doi.org/10.1016/j.bmcl.2012.07.049
W. Lehnert, Tetrahedron, 30, 301 (1974); https://doi.org/10.1016/S0040-4020(01)91461-9
B. Green, R.I. Crane, I.S. Khaidem, R.S. Leighton, S.S. Newaz and T.E. Smyser, J. Org. Chem., 50, 640 (1985); https://doi.org/10.1021/jo00205a016
P.S. Rao and R.V. Venkataratnam, Tetrahedron Lett., 32, 5821 (1991); https://doi.org/10.1016/S0040-4039(00)93564-0
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.K. Chakraborti, L. Sharma, R. Gulhane and Shivani, Tetrahedron, 59, 7661 (2003); https://doi.org/10.1016/j.tet.2003.08.007
G. Bartoli, L. Sambri, M. Bosco, M. Locatelli, E. Marcantoni and P. Melchiorre, Synlett, 239 (2004); https://doi.org/10.1055/s-2003-44974
G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi and L. Sambri, Eur. J. Org. Chem., 4611 (2003); https://doi.org/10.1002/ejoc.200300458
G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, P. Melchiorre and L. Sambri, Org. Lett., 7, 427 (2005); https://doi.org/10.1021/ol047704o
G. Bartoli, M. Locatelli, P. Melchiorre and L. Sambri, Eur. J. Org. Chem., 2037 (2007); https://doi.org/10.1002/ejoc.200600852
M. Lakshmi Kantam, B.M. Choudary, C.V. Reddy, K. Koteswara Rao, M. Lakshmi Kantam, B.M. Choudary, K. Koteswara Rao and F. Figueras, Chem. Commun., 1033 (1998); https://doi.org/10.1039/a707874i
J.R. Long, Chem. Health Saf., 9, 12 (2002); https://doi.org/10.1016/S1074-9098(02)00294-0
A.M. El-Awad, R.M. Gabr and M.M. Girgis, Thermochim. Acta, 184, 205 (1991); https://doi.org/10.1016/0040-6031(91)80024-D
S. Ghosh, J. Das and S. Chattopadhyay, Tetrahedron Lett., 52, 2869 (2011); https://doi.org/10.1016/j.tetlet.2011.03.123
A. Zicmanis and L. Anteina, Tetrahedron Lett., 55, 2027 (2014); https://doi.org/10.1016/j.tetlet.2014.02.035
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
M.L. Deb and P.J. Bhuyan, Tetrahedron Lett., 46, 6453 (2005); https://doi.org/10.1016/j.tetlet.2005.07.111
H. Xu, L. Pan, X. Fang, B. Liu, W. Zhang, M. Lu, Y. Xu, T. Ding and H. Chang, Tetrahedron Lett., 58, 2360 (2017); https://doi.org/10.1016/j.tetlet.2017.05.006
F. Bigi, L. Chesini, R. Maggi and G. Sartori, J. Org. Chem., 64, 1033 (1999); https://doi.org/10.1021/jo981794r
J. Azizian, F. Teimouri and M.R. Mohammadizadeh, Catal. Commun., 8, 1117 (2007); https://doi.org/10.1016/j.catcom.2006.06.002
T. Pirali, G.C. Tron, G. Masson and J. Zhu, Org. Lett., 9, 5275 (2007); https://doi.org/10.1021/ol7024372
P. Janvier, X. Sun, H. Bienayme and J. Zhu, J. Am. Chem. Soc., 124, 2560 (2002); https://doi.org/10.1021/ja017563a
D. Bonne, M. Dekhane and J. Zhu, Org. Lett., 6, 4771 (2004); https://doi.org/10.1021/ol0479388
G.W. Wang and C.S. Jia, Lett. Org. Chem., 3, 289 (2006); https://doi.org/10.2174/157017806776114568
H. Fang, Z. Ji-Ming, Y. Zhi-Jun and Z. Jian-Hua, Shandong Kexue, 23, 6 (2010).
M. Hosseini-Sarvari, Can. J. Chem., 87, 1122 (2009); https://doi.org/10.1139/V09-069
S. Genovese, F. Epifano, M.C. Marcotullio, C. Pelucchini and M. Curini, Tetrahedron Lett., 52, 3474 (2011); https://doi.org/10.1016/j.tetlet.2011.04.109