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Microwave Assisted Solvent-Free One Pot Biginelli Synthesis of Dihydropyrimidinone Compounds on Melamine-Formaldehyde as a Solid Support
Corresponding Author(s) : Ramin Rezaei
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
An effective one-pot synthesis of dihydropyrimidinonoes using Melamine-formaldehyde resin supported H+ (MFRH) as an inexpensive and readily available reagent through Biginelli condensation reaction of aldehyde, 1,3-dicarbonyl compounds and (thio)urea in conventional and under microwave irradiation conditions is described. Excellent yields, short reaction times for formation of the products and simple work-up are attractive features of this green protocol.
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- M. Larhed and A. Hallberg, Drug Discov. Today, 6, 406 (2001).
- J.L. Krstenansky and I. Cotterill, Curr. Opin. Drug Discov. Dev., 4, 454 (2000).
- C.O. Kappe, Tetrahedron, 49, 6937 (1993).
- G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. DiMarco, J.Z. Gougoutas, A. Hedberg, M.F. Malley, J.P. McCarthy, R. Zhang and S.J. Moreland, Med. Chem., 38, 119 (1995).
- L.E. Overman, M.H. Rabinowitz and P.A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995).
- T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999).
- P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
- B.C. O'Reilly and K.S. Atwal, Heterocycles, 26, 1185 (1987).
- B.K. Banik, A.T. Reddy, A. Datta and C. Mukhopadhyay, Tetrahedron Lett., 48, 7392 (2007).
- J.T. Li, J.F. Han, J.H. Yang and T.S. Li, Ultrason. Sonochem., 10, 119 (2003).
- J.J. Peng and Y.Q. Deng, Tetrahedron Lett., 42, 5917 (2001).
- Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000).
- S.J. Tu, F. Fang, C.B. Miao, H. Jiang, Y.J. Feng, D.Q. Shi and X.S. Wang, Tetrahedron Lett., 44, 6153 (2003).
- G. Sabitha, G.S.K.K. Reddy, K.B. Reddy and J.S. Yadav, Tetrahedron Lett., 44, 6497 (2003).
- F. Shirini, A. Yahyazadeh, M. Abedini and D.I. Langroodi, Bull. Korean Chem. Soc., 31, 1715 (2010).
- W.K. Su, J.J. Li, Z.G. Zheng and H.C. Shen, Tetrahedron Lett., 46, 6037 (2005).
- A. Debache, M. Amimour, A. Belfaitah, S. Rhouati and B.A. Carboni, Tetrahedron Lett., 49, 6119 (2008).
- N.Y. Fu, Y.F. Yuan, M.L. Pang, J.T. Wang and C. Peppe, Organomet. Chem., 672, 52 (2003).
- J. Azizian, A.A. Mohammadi,A.R. Karimi and M.R. Mohammadizadeh, Appl. Catal. A, 300, 85 (2006).
- P. Salehi, M. Dabiri, M.A. Zolfigol and M.A.B. Fard, Tetrahedron Lett., 44, 2889 (2003).
- K.A. Kumar, M. Kasthuraiah, C.S. Reddy and C.D. Reddy, Tetrahedron Lett., 42, 7873 (2001).
- N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor and B.M. Bhanage, J. Mol. Catal. A, 271, 14 (2007).
- R. Ghosh, S. Maiti and A. Chakraborty, J. Mol. Catal. A, 217, 47 (2004).
- N. Ahmed and J.E.V. Lier, Tetrahedron Lett., 48, 5407 (2007).
- M. Adib, K. Ghanbary, M. Mostofi and M.R. Ganjali, Molecules, 11, 649 (2006).
- H.N. Karade, M. Sathe and M.P. Kaushik, Molecules, 12, 1341 (2007).
- J. Cheng and D.Y. Qi, Chin. Chem. Lett., 18, 647 (2007).
- S.F. Hojati, M. Gholizadeh, M. Haghdoust and F. Shafiezadeh, Bull. Korean Chem. Soc., 31, 3238 (2010).
- (a) R. Rezaei, M.K. Mohammadi and N. Rastin, Chin. J. Chem., 28, 993 (2010); (b). R. Rezaei and M. Karami, Chin. Chem. Lett., 22, 815 (2011).
References
M. Larhed and A. Hallberg, Drug Discov. Today, 6, 406 (2001).
J.L. Krstenansky and I. Cotterill, Curr. Opin. Drug Discov. Dev., 4, 454 (2000).
C.O. Kappe, Tetrahedron, 49, 6937 (1993).
G.C. Rovnyak, S.D. Kimball, B. Beyer, G. Cucinotta, J.D. DiMarco, J.Z. Gougoutas, A. Hedberg, M.F. Malley, J.P. McCarthy, R. Zhang and S.J. Moreland, Med. Chem., 38, 119 (1995).
L.E. Overman, M.H. Rabinowitz and P.A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995).
T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999).
P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
B.C. O'Reilly and K.S. Atwal, Heterocycles, 26, 1185 (1987).
B.K. Banik, A.T. Reddy, A. Datta and C. Mukhopadhyay, Tetrahedron Lett., 48, 7392 (2007).
J.T. Li, J.F. Han, J.H. Yang and T.S. Li, Ultrason. Sonochem., 10, 119 (2003).
J.J. Peng and Y.Q. Deng, Tetrahedron Lett., 42, 5917 (2001).
Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000).
S.J. Tu, F. Fang, C.B. Miao, H. Jiang, Y.J. Feng, D.Q. Shi and X.S. Wang, Tetrahedron Lett., 44, 6153 (2003).
G. Sabitha, G.S.K.K. Reddy, K.B. Reddy and J.S. Yadav, Tetrahedron Lett., 44, 6497 (2003).
F. Shirini, A. Yahyazadeh, M. Abedini and D.I. Langroodi, Bull. Korean Chem. Soc., 31, 1715 (2010).
W.K. Su, J.J. Li, Z.G. Zheng and H.C. Shen, Tetrahedron Lett., 46, 6037 (2005).
A. Debache, M. Amimour, A. Belfaitah, S. Rhouati and B.A. Carboni, Tetrahedron Lett., 49, 6119 (2008).
N.Y. Fu, Y.F. Yuan, M.L. Pang, J.T. Wang and C. Peppe, Organomet. Chem., 672, 52 (2003).
J. Azizian, A.A. Mohammadi,A.R. Karimi and M.R. Mohammadizadeh, Appl. Catal. A, 300, 85 (2006).
P. Salehi, M. Dabiri, M.A. Zolfigol and M.A.B. Fard, Tetrahedron Lett., 44, 2889 (2003).
K.A. Kumar, M. Kasthuraiah, C.S. Reddy and C.D. Reddy, Tetrahedron Lett., 42, 7873 (2001).
N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor and B.M. Bhanage, J. Mol. Catal. A, 271, 14 (2007).
R. Ghosh, S. Maiti and A. Chakraborty, J. Mol. Catal. A, 217, 47 (2004).
N. Ahmed and J.E.V. Lier, Tetrahedron Lett., 48, 5407 (2007).
M. Adib, K. Ghanbary, M. Mostofi and M.R. Ganjali, Molecules, 11, 649 (2006).
H.N. Karade, M. Sathe and M.P. Kaushik, Molecules, 12, 1341 (2007).
J. Cheng and D.Y. Qi, Chin. Chem. Lett., 18, 647 (2007).
S.F. Hojati, M. Gholizadeh, M. Haghdoust and F. Shafiezadeh, Bull. Korean Chem. Soc., 31, 3238 (2010).
(a) R. Rezaei, M.K. Mohammadi and N. Rastin, Chin. J. Chem., 28, 993 (2010); (b). R. Rezaei and M. Karami, Chin. Chem. Lett., 22, 815 (2011).