Copyright (c) 2023 Santosh Pore
This work is licensed under a Creative Commons Attribution 4.0 International License.
Natural Surfactant Mediated Synthesis of 4-Aryl Substituted 3,4-Dihydropyrimidinones
Corresponding Author(s) : Santosh B. Pore
Asian Journal of Chemistry,
Vol. 35 No. 12 (2023): Vol 35 Issue 12, 2023
Abstract
Present work describes the synthesis of 4-aryl substituted 3,4-dihydropyrimidinones (DHPMs) using aqueous extract of pericarp of Sapindus trifoliatus fruit as a green catalyst. The reaction is a one-pot reaction, similar to classical Biginelli reaction employing an aromatic aldehyde, urea and active methylene compound (ethyl acetoacetate) as substrates. Desired DHPMs were yielded within 2 h at room temperature. The key advantage of the present strategy was its low dependence on organic solvents as green synthesis.
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- C.O. Kappe, Tetrahedron, 49, 6937 (1993); https://doi.org/10.1016/S0040-4020(01)87971-0
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- L. Heys, C.G. Moore and P.J. Murphy, Chem. Soc. Rev., 29, 57 (2000); https://doi.org/10.1039/a903712h
- R. S. Varma, Org. Chem. Highlights (2007); https://www.organic-chemistry.org/Highlights/2007/01February.shtm
- C.R. Strauss and R.W. Trainor, Aust. J. Chem., 48, 1665 (1995); https://doi.org/10.1071/CH9951665
- P. Wipf and A. Cunningham, Tetrahedron Lett., 36, 7819 (1995); https://doi.org/10.1016/0040-4039(95)01660-A
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References
C.O. Kappe, Tetrahedron, 49, 6937 (1993); https://doi.org/10.1016/S0040-4020(01)87971-0
K. Atwal, G.C. Rovnyak, J. Schwartz, S. Moreland, A. Hedberg, J.Z. Gougoutas, M.F. Malley and D.M. Floyd, J. Med. Chem., 33, 1510 (1990); https://doi.org/10.1021/jm00167a035
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); https://doi.org/10.1021/jm00106a048
G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M.F. Malley, J. Med. Chem., 35, 3254 (1992); https://doi.org/10.1021/jm00095a023
J.C. Barrow, P.G. Nantermet, H.G. Selnick, K.L. Glass, K.E. Rittle, K.F. Gilbert, T.G. Steele, C.F. Homnick, R.M. Freidinger, R.W. Ransom, P. Kling, D. Reiss, T.P. Broten, T.W. Schorn, R.S.L. Chang, S.S. O’Malley, T.V. Olah, J.D. Ellis, A. Barrish, K. Kassahun, P. Leppert, D. Nagarathnam and C. Forray, J. Med. Chem., 43, 2703 (2000); https://doi.org/10.1021/jm990612y
D.W. McKinstry and E.H. Reading, J. Franklin Inst., 237, 422 (1944); https://doi.org/10.1016/S0016-0032(44)90972-5
E.W. Hurst and R. Hull, J. Med. Pharm. Chem., 3, 215 (1961); https://doi.org/10.1021/jm50015a002
M.C. Jara, A.C. Assunção-Silva, M. Ritter, A.F. da Silva, C.L. Gonçalves, P.R. dos Santos, L.S. Borja, C.M.P. de Pereira and P. da Silva Nascente, Front. Microbiol., 13, 743213 (2022); https://doi.org/10.3389/fmicb.2022.743213
R.S. Kirby, S. Ballard, J. Blagg and D. Fox, Benign Prostatic Hyperplasia, Gower Medical, London (1993).
C.G. Roehrborn, J.E. Oesterling, S. Auerbach, S.A. Kaplan, L. Keith Lloyd, D.F. Milam and R.J. Padley, Urology, 47, 159 (1996); https://doi.org/10.1016/S0090-4295(99)80409-9
L. Ismaili, A. Nadaradjane, L. Nicod, C. Guyon, A. Xicluna, J.F. Robert and B. Refouvelet, Eur. J. Med. Chem., 43, 1270 (2008); https://doi.org/10.1016/j.ejmech.2007.07.012
E. Rafiee and H. Jafari, Bioorg. Med. Chem. Lett., 16, 2463 (2006); https://doi.org/10.1016/j.bmcl.2006.01.087
V. Polshettiwar and R.S. Varma, Tetrahedron Lett., 48, 7343 (2007); https://doi.org/10.1016/j.tetlet.2007.08.031
V.S. Palekar and S.R. Shukla, Green Chem. Lett. Rev., 1, 185 ( (2008); https://doi.org/10.1080/17518250802541490
O.M. Singh, S.J. Singh, M.B. Devi, L.N. Devi, N.I. Singh and S.-G. Lee, Bioorg. Med. Chem. Lett., 18, 6462 (2008); https://doi.org/10.1016/j.bmcl.2008.10.063
X. Jing, Z. Li, X. Pan, Q. Wang, C. Yan and H. Zhu, Synth. Commun., 39, 3796 (2009); https://doi.org/10.1080/00397910902838896
J.-P. Wan, C. Wang and Y. Pan, Tetrahedron, 67, 922 (2011); https://doi.org/10.1016/j.tet.2010.12.011
K. Bahrami, M.M. Khodaei and A. Farrokhi, Synth. Commun., 39, 1801 (2009); https://doi.org/10.1080/00397910802592874
R.J. Schmidt, L.J. Lombardo, S.C. Traeger and D.K. Williams, Tetrahedron Lett., 49, 3009 (2008); https://doi.org/10.1016/j.tetlet.2008.02.162
R. Zheng, X. Wang, H. Xu and J. Du, Synth. Commun., 36, 1503 (2006); https://doi.org/10.1080/00397910600588488
P. Srivastava and L. Engman, Tetrahedron Lett., 51, 1149 (2010); https://doi.org/10.1016/j.tetlet.2009.12.104
Z. Fang and Y. Lam, Tetrahedron, 67, 1294 (2011); https://doi.org/10.1016/j.tet.2010.11.075
B.K. Banik, A.T. Reddy, A. Datta and C. Mukhopadhyay, Tetrahedron Lett., 48, 7392 (2007); https://doi.org/10.1016/j.tetlet.2007.08.007
S. Pore, G. Rashinkar, K. Mote and R. Salunkhe, Chem. Biodivers., 7, 1796 (2010); https://doi.org/10.1002/cbdv.200900272
L. Heys, C.G. Moore and P.J. Murphy, Chem. Soc. Rev., 29, 57 (2000); https://doi.org/10.1039/a903712h
R. S. Varma, Org. Chem. Highlights (2007); https://www.organic-chemistry.org/Highlights/2007/01February.shtm
C.R. Strauss and R.W. Trainor, Aust. J. Chem., 48, 1665 (1995); https://doi.org/10.1071/CH9951665
P. Wipf and A. Cunningham, Tetrahedron Lett., 36, 7819 (1995); https://doi.org/10.1016/0040-4039(95)01660-A
A. Shutalev, E. Kishko, N. Sivova and A. Kuznetsov, Molecules, 3, 100 (1998); https://doi.org/10.3390/30300100
G. Rashinkar and R. Salunkhe, J. Mol. Catal. Chem., 316, 146 (2010); https://doi.org/10.1016/j.molcata.2009.10.013
G. Rashinkar, S. Pore and R. Salunkhe, Phosphorus Sulfur Silicon Relat. Elem., 184, 1750 (2009); https://doi.org/10.1080/10426500802339865
C.O. Kappe, Acc. Chem. Res., 33, 879 (2000); https://doi.org/10.1021/ar000048h
Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000); https://doi.org/10.1021/jo9919052