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Metals as Renewable Catalysts in MCR Synthesis of Dihydropyrimidinones
Corresponding Author(s) : Muhammad Naeem Khan
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
Various metals (Cu, Fe, Al and Zn) have been successfully employed in the MCR of aryl carbaldehydes, ethyl acetoacetate and urea to give respective dihydropyrimidinones in good to excellent yields. The catalysts in these reactions are easily recovered and used many times without losing its catalytic activity. The products were duly characterized through their spectral analysis.
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- C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
- P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
- K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg and B.C. O’Reilly, J. Med. Chem., 34, 806 (1991); doi:10.1021/jm00106a048.
- C.O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000); doi:10.1016/S0223-5234(00)01189-2.
- (a) T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999); doi:10.1126/science.286.5441.971; (b) T.M. Kapoor, T.U. Mayer, M.L. Coughlin and T.J. Mitchison, J. Cell Biol., 150, 975 (2000); doi:10.1083/jcb.150.5.975.
- E.W. Hurst and R. Hull, J. Med. Pharm. Chem., 3, 215 (1961); doi:10.1021/jm50015a002.
- M. Ashok, B.S. Holla and N.S. Kumari, Eur. J. Med. Chem., 42, 380 (2007); doi:10.1016/j.ejmech.2006.09.003.
- S.W. Fewell, C.M. Smith, M.A. Lyon, T.P. Dumitrescu, P. Wipf, B.W. Day and J.L. Brodsky, J. Biol. Chem., 279, 51131 (2004); doi:10.1074/jbc.M404857200.
- A.M. Magerramov, M.M. Kurbanova, R.T. Abdinbekova, I.A. Rzaeva, V.M. Farzaliev and M.A. Allakhverdiev, Russ. J. Appl. Chem., 79, 787 (2006); doi:10.1134/S107042720605017X.
- C.O. Kappe and S.F. Falsone, Synlett, 718 (1998); doi:10.1055/s-1998-1764.
- Y. Zhu, Y. Pan and S. Huang, Synth. Commun., 34, 3167 (2004); doi:10.1081/SCC-200028607.
- G. Sabitha, G.S. Kumar Reddy, C.S. Reddy and J.S. Yadav, Synlett, 858 (2003); doi:10.1055/s-2003-38734.
- I. Cepanec, M. Litvić, A. Bartolinćić and M. Lovrić, Tetrahedron, 61, 4275 (2005); doi:10.1016/j.tet.2005.02.059.
- (a) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 2886 (1933); doi:10.1021/ja01334a043; (b) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933); doi:10.1021/ja01336a054.
- E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); doi:10.1021/jo970846u.
- J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); doi:10.1016/S0040-4039(00)01645-2.
- D.S. Bose, L. Fatima and H.B. Mereyala, J. Org. Chem., 68, 587 (2003); doi:10.1021/jo0205199.
- B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); doi:10.1021/jo000711f.
- K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Synlett, 863 (2001); doi:10.1055/s-2001-14587.
- A.S. Paraskar, G.K. Dewkar and A. Sudalai, Tetrahedron Lett., 44, 3305 (2003); doi:10.1016/S0040-4039(03)00619-1.
- G. Maiti, P. Kundu and C. Guin, Tetrahedron Lett., 44, 2757 (2003); doi:10.1016/S0040-4039(02)02859-9.
- N.Y. Fu, Y.F. Yuan, Z. Cao, S.W. Wang, J.T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); doi:10.1016/S0040-4020(02)00455-6.
- A.K. Bose, M.S. Manhas, S. Pednekar, S.N. Ganguly, H. Dang, W. He and A. Mandadi, Tetrahedron Lett., 46, 1901 (2005); doi:10.1016/j.tetlet.2005.01.087.
- J.C. Rodriguez-Dominguez, D. Bernardi and G. Kirsch, Tetrahedron Lett., 48, 5777 (2007); doi:10.1016/j.tetlet.2007.06.104.
- E. Rafiee and H. Jafari, Bioorg. Med. Chem. Lett., 16, 2463 (2006); doi:10.1016/j.bmcl.2006.01.087.
- A. Kumar and R.M. Maurya, Tetrahedron Lett., 48, 4569 (2007); doi:10.1016/j.tetlet.2007.04.130.
- A. Karamat, M.A. Khan and A. Sharif, J. Chinese Chem. Soc., 57, 1099 (2010); doi:10.1002/jccs.201000155; S. Imtiaz, M.A. Khan, A. Sharif, E. Ahmed, W.-O. Lin and M.A. Munawar, J. Chinese Chem. Soc., 59, 1446 (2012); doi:10.1002/jccs.201100472; A.M. Zafar, S. Qureshi, M.N. Khan, M. Azad, M.A. Munawar and M.A. Khan, Asian J. Chem., 25, 3244 (2013); doi:10.14233/ajchem.2013.13607; S. Noreen, S. Perveen, M.N. Khan, A. Nazeer, M.A. Khan, M.A. Munawar, R. Babar, F. Suhail, M. Azad, A.M.R. Bernardino and M.S. Dos Santos, Asian J. Chem., 25, 4770 (2013); doi:10.14233/ajchem.2013.14094.
- K. Folkers, H.J. Harwood and F.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932); doi:10.1021/ja01348a040.
- Y. Yu, D. Liu, C. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007); doi:10.1016/j.bmcl.2006.12.068.
- J.S. Yadav, B.V. Subba Reddy, P. Sridhar, J.S.S. Reddy, K. Nagaiah, N. Lingaiah and P.S. Saiprasad, Eur. J. Org. Chem., 552 (2004); doi:10.1002/ejoc.200300559.
References
C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg and B.C. O’Reilly, J. Med. Chem., 34, 806 (1991); doi:10.1021/jm00106a048.
C.O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000); doi:10.1016/S0223-5234(00)01189-2.
(a) T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999); doi:10.1126/science.286.5441.971; (b) T.M. Kapoor, T.U. Mayer, M.L. Coughlin and T.J. Mitchison, J. Cell Biol., 150, 975 (2000); doi:10.1083/jcb.150.5.975.
E.W. Hurst and R. Hull, J. Med. Pharm. Chem., 3, 215 (1961); doi:10.1021/jm50015a002.
M. Ashok, B.S. Holla and N.S. Kumari, Eur. J. Med. Chem., 42, 380 (2007); doi:10.1016/j.ejmech.2006.09.003.
S.W. Fewell, C.M. Smith, M.A. Lyon, T.P. Dumitrescu, P. Wipf, B.W. Day and J.L. Brodsky, J. Biol. Chem., 279, 51131 (2004); doi:10.1074/jbc.M404857200.
A.M. Magerramov, M.M. Kurbanova, R.T. Abdinbekova, I.A. Rzaeva, V.M. Farzaliev and M.A. Allakhverdiev, Russ. J. Appl. Chem., 79, 787 (2006); doi:10.1134/S107042720605017X.
C.O. Kappe and S.F. Falsone, Synlett, 718 (1998); doi:10.1055/s-1998-1764.
Y. Zhu, Y. Pan and S. Huang, Synth. Commun., 34, 3167 (2004); doi:10.1081/SCC-200028607.
G. Sabitha, G.S. Kumar Reddy, C.S. Reddy and J.S. Yadav, Synlett, 858 (2003); doi:10.1055/s-2003-38734.
I. Cepanec, M. Litvić, A. Bartolinćić and M. Lovrić, Tetrahedron, 61, 4275 (2005); doi:10.1016/j.tet.2005.02.059.
(a) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 2886 (1933); doi:10.1021/ja01334a043; (b) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933); doi:10.1021/ja01336a054.
E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); doi:10.1021/jo970846u.
J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); doi:10.1016/S0040-4039(00)01645-2.
D.S. Bose, L. Fatima and H.B. Mereyala, J. Org. Chem., 68, 587 (2003); doi:10.1021/jo0205199.
B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); doi:10.1021/jo000711f.
K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Synlett, 863 (2001); doi:10.1055/s-2001-14587.
A.S. Paraskar, G.K. Dewkar and A. Sudalai, Tetrahedron Lett., 44, 3305 (2003); doi:10.1016/S0040-4039(03)00619-1.
G. Maiti, P. Kundu and C. Guin, Tetrahedron Lett., 44, 2757 (2003); doi:10.1016/S0040-4039(02)02859-9.
N.Y. Fu, Y.F. Yuan, Z. Cao, S.W. Wang, J.T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); doi:10.1016/S0040-4020(02)00455-6.
A.K. Bose, M.S. Manhas, S. Pednekar, S.N. Ganguly, H. Dang, W. He and A. Mandadi, Tetrahedron Lett., 46, 1901 (2005); doi:10.1016/j.tetlet.2005.01.087.
J.C. Rodriguez-Dominguez, D. Bernardi and G. Kirsch, Tetrahedron Lett., 48, 5777 (2007); doi:10.1016/j.tetlet.2007.06.104.
E. Rafiee and H. Jafari, Bioorg. Med. Chem. Lett., 16, 2463 (2006); doi:10.1016/j.bmcl.2006.01.087.
A. Kumar and R.M. Maurya, Tetrahedron Lett., 48, 4569 (2007); doi:10.1016/j.tetlet.2007.04.130.
A. Karamat, M.A. Khan and A. Sharif, J. Chinese Chem. Soc., 57, 1099 (2010); doi:10.1002/jccs.201000155; S. Imtiaz, M.A. Khan, A. Sharif, E. Ahmed, W.-O. Lin and M.A. Munawar, J. Chinese Chem. Soc., 59, 1446 (2012); doi:10.1002/jccs.201100472; A.M. Zafar, S. Qureshi, M.N. Khan, M. Azad, M.A. Munawar and M.A. Khan, Asian J. Chem., 25, 3244 (2013); doi:10.14233/ajchem.2013.13607; S. Noreen, S. Perveen, M.N. Khan, A. Nazeer, M.A. Khan, M.A. Munawar, R. Babar, F. Suhail, M. Azad, A.M.R. Bernardino and M.S. Dos Santos, Asian J. Chem., 25, 4770 (2013); doi:10.14233/ajchem.2013.14094.
K. Folkers, H.J. Harwood and F.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932); doi:10.1021/ja01348a040.
Y. Yu, D. Liu, C. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007); doi:10.1016/j.bmcl.2006.12.068.
J.S. Yadav, B.V. Subba Reddy, P. Sridhar, J.S.S. Reddy, K. Nagaiah, N. Lingaiah and P.S. Saiprasad, Eur. J. Org. Chem., 552 (2004); doi:10.1002/ejoc.200300559.