Abstract
An efficient one-pot multicomponent synthesis multicomponent synthesis of 3,4- dihydropyrimidin- 2(1H)-ones has been developed from aldehyde bisulfite adducts, ethyl acetoacetate and urea using recyclable polymer-supported sulfonic acid catalyst. This new method provides several advantages over the previous synthesis, including high product yields, commercially viable, minimal workup operations and sustainable chemical practices.
Keywords: 3, 4-dihydropyrimidin-2(1H)-ones, wang resin-supported sulfonic acid, recyclable catalyst, aldehyde bisulfite adduct, biginelli reaction, multicomponent synthesis.
Graphical Abstract
[http://dx.doi.org/10.1016/S0040-4020(01)87971-0]
(b) Kappe, C.O. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
(c) Kappe, C.O. Eur. J. Med. Chem., 2000, 35(12), 1043-1052.
[http://dx.doi.org/10.1016/S0223-5234(00)01189-2] [PMID: 11248403]
[http://dx.doi.org/10.1016/j.ejmech.2006.09.003] [PMID: 17070617]
[http://dx.doi.org/10.1016/j.bmcl.2004.01.039] [PMID: 15026060]
[http://dx.doi.org/10.1134/S107042720605017X]
[http://dx.doi.org/10.1097/00005344-199508000-00015] [PMID: 7475054]
[http://dx.doi.org/10.1021/jm00001a017] [PMID: 7837222]
(b) Sidler, D.R.; Larsen, R.D.; Chartrain, M.; Ikemoto, N.; Roberge, C.M.; Taylor, C.S.; Li, W.; Bills, G.F. PCT Int. Appl. WO, 1999, 99/07695, 18.
[http://dx.doi.org/10.1039/a903712h]
[http://dx.doi.org/10.1021/jo00110a021]
[http://dx.doi.org/10.1039/c39950001369]
(b) Snider, B.B.; Chen, J.; Patil, A.D.; Freyer, A.J. Tetrahedron Lett., 1996, 37(39), 6977-6980.
[http://dx.doi.org/10.1016/0040-4039(96)01575-4]
(c) Kappe, C.O.; Falsone, S.F. Synlett, 1998, (07), 718-720.
[http://dx.doi.org/10.1055/s-1998-1764]
[http://dx.doi.org/10.1021/jo000711f] [PMID: 10987976]
(b) Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem., 2000, 65(12), 3864-3868.
[http://dx.doi.org/10.1021/jo9919052] [PMID: 10864778]
(c) Lin, H.; Ding, J.; Chen, X.; Zhang, Z. Molecules, 2000, 5(12), 1240-1243.
[http://dx.doi.org/10.3390/51201240]
(d) Lu, J.; Ma, H. Synlett, 2000, (1), 63-64.
(e) Yadav, J.S.; Reddy, B.V.S.; Reddy, E.J.; Ramalingam, T. J. Chem. Res. (S), 2000, 2000(7), 354-355.
[http://dx.doi.org/10.3184/030823400103167633]
(f) Stefani, H.A.; Gatti, P.M. Synth. Commun., 2000, 30(12), 2165-2173.
[http://dx.doi.org/10.1080/00397910008087395]
[http://dx.doi.org/10.1055/s-2001-15229]
(b) Kumar, K.A.; Kasthuraiah, M.; Reddy, C.S.; Reddy, C.D. Tetrahedron Lett., 2001, 42(44), 7873-7875.
[http://dx.doi.org/10.1016/S0040-4039(01)01603-3]
(c) Peng, J.; Deny, Y. Tetrahedron Lett., 2001, 42(34), 5917-5919.
[http://dx.doi.org/10.1016/S0040-4039(01)01139-X]
(d) Dondoni, A.; Massi, A. Tetrahedron Lett., 2001, 42(45), 7975-7978.
[http://dx.doi.org/10.1016/S0040-4039(01)01728-2]
[http://dx.doi.org/10.1016/S0040-4039(02)00280-0]
(b) Lu, J.; Bai, Y. Synthesis, 2002, 2002(04), 466-470.
[http://dx.doi.org/10.1055/s-2002-20956]
(c) Jin, T.; Zhang, S.; Zhang, S.; Guo, J.; Li, T. J. Chem. Res. (S), 2002, 2002(1), 37-39.
[http://dx.doi.org/10.3184/030823402103170394]
[http://dx.doi.org/10.1055/s-2003-38734]
[http://dx.doi.org/10.1016/j.tetlet.2013.09.105]
[http://dx.doi.org/10.1016/j.molcata.2013.07.001]
[http://dx.doi.org/10.1073/pnas.96.21.11878] [PMID: 10518544]
[http://dx.doi.org/10.1039/c3cc41588k] [PMID: 23646348]
[http://dx.doi.org/10.1016/j.tet.2008.12.079]
[http://dx.doi.org/10.1002/hc.20352]
[http://dx.doi.org/10.1016/j.cej.2019.02.016]
(b) Wenlei, X.; Hao, W. Renew. Energy., 2020, 145, 1709-1719.
[http://dx.doi.org/10.1016/j.renene.2019.07.092]
(c) Wenlei, X.; Hao, W. J. Ind. Eng. Chem., 2020, 87, 162-172.
[http://dx.doi.org/10.1016/j.jiec.2020.03.033]
(d) Eskandar, K.; Nadia, K.; Maliheh, M.H. J. Mol. Catal. Chem., 2015, 397, 68-75.
[http://dx.doi.org/10.1016/j.molcata.2014.10.026]
(e) Wei, L.; Christopher, W.J. ACS Catal., 2011, 1(7), 674-681.
[http://dx.doi.org/10.1021/cs2001175]
(f) Raimondo, M.; Raveendran, S.N.; Veronica, S.; Giovanni, M.; Franca, B.; Gadi, R. Beilstein J. Org. Chem., 2016, 12, 2173-2180.
[http://dx.doi.org/10.3762/bjoc.12.207] [PMID: 27829924]
[http://dx.doi.org/10.1016/j.tetlet.2015.06.004]