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Biginelli Reaction-Carboxylic Acids as Catalysts
Corresponding Author(s) : Muhammad Naeem Khan
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
Mono and dicarboxylic acids were found to be excellent catalysts for the synthesis of dihydropyrimidones/thiones. These are presented as alternate and cheap catalysts for the multicomponent reactions.
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- D.J. Brown, In eds.: A.R. Katritzky and C. W Rees, In Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford (1984).
- P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
- G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J.P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 38, 119 (1995).
- G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O' Reilly, J. Schwarz and M.F. Malley, J. Med. Chem., 35, 3254 (1992).
- S.D. Sidler, R.D. Larsen, M. Chartrain, N. Ikemoto, C.M. Roberge, C.S. Taylor, W. Li and G.F. Bills, PCT. Int. Appl. WO# 9906795 (1999).
- C.O. Kappe and A. Stadler, Org. React. A, 65, 1 (2004).
- K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Synlett, 863 (2001).
- J. Lu and Y. Bai, Synthesis, 466 (2002).
- C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.V.N. Reddy, Tetrahedron Lett., 43, 2657 (2002).
- C. Liu, J. Wang and Y. Li, J. Mol. Catal. A, 258, 367 (2006).
- L. Wang, C. Qian, H. Tian and Y. Ma, Synth. Commun., 33, 1459 (2003).
- P. Salehi, M. Dabiri, M.A. Zolfigol and M.A.B. Fardi, Tetrahedron Lett., 44, 2889 (2003).
- M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc. Perkin Trans. 1, 1845 (2002).
- M. Abdollahi and Z. Zaghaghi, Chem. Papers, 63, 97 (2009).
- I. Saxena, D.C. Borah and J.C. Sarma, Tetrahedron Lett., 46, 1159 (2005).
- X. Feng, J.-J. Wang and Y.-P. Tian, Synth. Commun., 38, 1299 (2008).
- D. Shobha, M.A. Chari, P. Sadanandam and K. Mukkanti, J. Heterocycl. Chem., 45, 1225 (2008).
- D. Russowsky, F.A. Lopes, V.S.S. da Silva, K.F.S. Canto, M.G.M. D` Oca and M.N. Godoi, J. Braz. Chem. Soc., 15, 165 (2004).
- A. Debache, M. Amimour, A. Belfaitah, S. Rhouati and B. Carboni, Tetrahedron Lett., 49, 6119 (2008).
- F. Tamaddon, Z. Razmi and A.A. Jafar, Tetrahedron Lett., 51, 1187 (2010).
- J. Peng and Y. Deng, Tetrahedron Lett., 42, 5917 (2001).
- E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998).
- J. Lu and H. Ma, Synlett, 63 (2000).
- Y. Yu, D. Liu, C. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007).
- S. Gore, S. Baskaran and B. Koenig, Green Chem., 13, 1009 (2011).
- J. Wichmann, G. Adam, S. Kolczewski, V. Mutel and T. Woltering, Bioorg. Med. Chem. Lett., 9, 1573 (1999).
References
D.J. Brown, In eds.: A.R. Katritzky and C. W Rees, In Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford (1984).
P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J.P. McCarthy, R. Zhang and S. Moreland, J. Med. Chem., 38, 119 (1995).
G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O' Reilly, J. Schwarz and M.F. Malley, J. Med. Chem., 35, 3254 (1992).
S.D. Sidler, R.D. Larsen, M. Chartrain, N. Ikemoto, C.M. Roberge, C.S. Taylor, W. Li and G.F. Bills, PCT. Int. Appl. WO# 9906795 (1999).
C.O. Kappe and A. Stadler, Org. React. A, 65, 1 (2004).
K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Synlett, 863 (2001).
J. Lu and Y. Bai, Synthesis, 466 (2002).
C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.V.N. Reddy, Tetrahedron Lett., 43, 2657 (2002).
C. Liu, J. Wang and Y. Li, J. Mol. Catal. A, 258, 367 (2006).
L. Wang, C. Qian, H. Tian and Y. Ma, Synth. Commun., 33, 1459 (2003).
P. Salehi, M. Dabiri, M.A. Zolfigol and M.A.B. Fardi, Tetrahedron Lett., 44, 2889 (2003).
M. Kidwai, S. Saxena, R. Mohan and R. Venkataramanan, J. Chem. Soc. Perkin Trans. 1, 1845 (2002).
M. Abdollahi and Z. Zaghaghi, Chem. Papers, 63, 97 (2009).
I. Saxena, D.C. Borah and J.C. Sarma, Tetrahedron Lett., 46, 1159 (2005).
X. Feng, J.-J. Wang and Y.-P. Tian, Synth. Commun., 38, 1299 (2008).
D. Shobha, M.A. Chari, P. Sadanandam and K. Mukkanti, J. Heterocycl. Chem., 45, 1225 (2008).
D. Russowsky, F.A. Lopes, V.S.S. da Silva, K.F.S. Canto, M.G.M. D` Oca and M.N. Godoi, J. Braz. Chem. Soc., 15, 165 (2004).
A. Debache, M. Amimour, A. Belfaitah, S. Rhouati and B. Carboni, Tetrahedron Lett., 49, 6119 (2008).
F. Tamaddon, Z. Razmi and A.A. Jafar, Tetrahedron Lett., 51, 1187 (2010).
J. Peng and Y. Deng, Tetrahedron Lett., 42, 5917 (2001).
E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998).
J. Lu and H. Ma, Synlett, 63 (2000).
Y. Yu, D. Liu, C. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007).
S. Gore, S. Baskaran and B. Koenig, Green Chem., 13, 1009 (2011).
J. Wichmann, G. Adam, S. Kolczewski, V. Mutel and T. Woltering, Bioorg. Med. Chem. Lett., 9, 1573 (1999).