N-Sulfonic acid poly(4-vinylpyridinium) chloride as a highly efficient and reusable catalyst for the Biginelli reaction

Chinese Chemical Letters

Volumn 25, Issue 1, 2014, Pages 111-114

  Shirini, Frahad ^a   Abedini, Masoumeh ^a   Pourhasan Kisomi, Reyhaneh ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

3,4 Dihydropyrimidin 2(1H) ones; Biginelli reaction; N sulfonic acid poly(4 vinylpyridinium) chloride (NSPVPC); Reusable catalyst; Solvent free conditions

Indexed keywords

EID: 84892601066     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.09.005     Document Type: Article

References (33)

1. C.O. Kappe 100 Years of the Biginelli dihydropyrimidine synthesis Tetrahedron 49 1993 6963-6963
2. C.O. Kappe Biologically active dihydripyrimidones of the Bignelli-type. A literature survey Eur. J. Med. Chem. 35 2000 1043 1052
3. C.O. Kappe, D. Kummar, and R.S. Varma Microwave-assisted high-speed parallel synthesis of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones using a solventless Biginelli condensation protocol Synthesis 1999 1799 1803
4. K.S. Atwal, G.C. Rovnyak, and S.D. Kimball et al. Dihydropyrimidine calcium channel blockers. 2. 3-substituted-4-aryl-1,4-dihydro-6-methyl-5- pyrimidine carboxylic acid esters as potent mimics of dihydropyridines J. Med. Chem. 33 1990 2629 2635
5. C.O. Kappe, O.V. Shishkin, G. Uray, and P. Verdino X-ray structure, conformational analysis, enantioseparation and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol Tetrahedron 56 2000 1859 1862
6. G.C. Rovynal, S.D. Kimball, and B. Beyer et al. Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators J. Med. Chem. 38 1995 119 129
7. P. Biginelli Aldehyde-urea derivatives of aceto- and oxaloacetic acids Gazz. Chim. Ital. 23 1893 360 413
8. M. Tajbakhsh, Y. Ranjbar, A. Masuodi, and S. Khaksar A simple and environmentally benign protocol for Biginelli reactions catalyzed by silica-bonded S-sulfonic acid Chin. J. Catal. 33 2012 1542 1545
9. M. Moghaddas, A. Davoodnia, M.M. Heravi, and N. Tavakoli-Hoseini Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones Chin. J. Catal. 33 2012 706 710
10. 3H nanocomposites as an efficient acid catalyst for the Biginelli reaction Appl. Clay Sci. 55 2012 1 9
11. 3H): a mild, reusable and highly efficient heterogeneous catalyst for the Biginelli reaction Chin. Chem. Lett. 19 2008 1435 1439
12. S.R. Mistry, and K.C. Maheria Synthesis of diarylpyrimidinones (DAPMs) using large pore zeolites J. Mol. Catal. A: Chem. 355 2012 210 215
13. S.R. Narahari, B.R. Reguri, O. Gudaparthi, and K. Mukkanti Synthesis of dihydropyrimidinones via Biginelli multi-component reaction Tetrahedron Lett. 53 2012 1543 1545
14. A. Dondoni, and A. Massi Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions. A green chemistry approach to the Biginelli reaction Tetrahedron Lett. 42 2001 7975 7978
15. 2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones Tetrahedron Lett. 44 2003 3305 3308
16. H. Xu, and Y.G. Wang A rapid and efficient Biginelli reaction catalyzed by zinc triflate Chin. J. Chem. 21 2003 327 331
17. R. Varala, M.M. Alam, and S.R. Adapa Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2 (1H)-ones: an improved protocol for the Biginelli reaction Synth. Lett. 2003 67 70
18. R.W. Zheng, X.X. Wang, H. Xu, and J.X. Du Brønsted acidic ionic liquid: An efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones Synth. Commun. 36 2006 1503 1513
19. M. Li, W.S. Guo, L.R. Wen, Y.F. Li, and H.Z. Yang One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products J. Mol. Catal. A 258 2006 133 138
20. J.J. Peng, and Y.Q. Deng Ionic liquids catalyzed Biginelli reaction under solvent-free conditions Tetrahedron Lett. 42 2001 5917 5919
21. F. Shirini, M.A. Zolfigol, and J. Albadi Melamine trisulfonic acid: a new, efficient and recyclable catalyst for the synthesis of 3,4- dihydropyrimidin-2(1H)-ones/thiones in the absence of solvent Chin. Chem. Lett. 22 2011 318 321
22. 2O as an efficient reagent for the solvent-free synthesis of 3,4-dihydropyrimidin-2-(1H)-ones Synth. Commun. 36 2006 2307 2310
23. F. Shirini, K. Marjani, and H.T. Nahzomi Silica triflate as an efficient catalyst for the solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones Arkivoc 1 2007 51 57
24. 3 as an efficient catalyst for the preparation of 3,4-dihydropyrimidin-2(1H)-ones in solution and under solvent-free conditions J. Iran. Chem. Soc. 5 2008 96 99
25. F. Shirini, M.A. Zolfigol, and E. Mollarazi An efficient method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) using trichloroisocyanuric acid (TCCA) under solvent-free conditions Lett. Org. Chem. 2 2005 718 720
26. F. Shirini, and O.G. Jolodar Introduction of N-sulfonic acid poly(4-vinylpyridinum) chloride as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes J. Mol. Catal. A: Chem. 356 2012 61 69
27. F. Shirini, N.G. Khaligh, and O.G. Jolodar N-Sulfonic acid poly(4-vinylpyridinium) chloride: an efficient and reusable solid acid catalyst in N-Boc protection of amines J. Iran. Chem. Soc. 10 2013 181 188
28. F. Shirini, N.G. Khaligh, and O.G. Jolodar An efficient and practical synthesis of bis(indolyl)methanes catalyzed by N-sulfonic acid poly(4-vinylpyridinium) chloride Dyes Pigments 98 2013 290 296
29. 40/Pip-SBA-15: a novel reusable organic-inorganic hybrid material as potent Lewis acid catalyst for one-pot solvent-free synthesis of 3,4-dihydropyrimidinones J. Mol. Catal. A: Chem. 366 2013 266 274
30. 4] Arabian J. Chem. 5 2012 485 488
31. A.R. Hajipour, and M. Seddighi Pyridinium-based Brønsted acidic ionic liquid as a highly efficient catalyst for one-pot synthesis of dihydropyrimidinones Synth. Commun. 42 2012 227 235
32. 3H as an efficient catalyst for 3,4-dihydropyrimidones via Biginelli reaction Catal. Commun. 10 2009 1146 1148
33. F. Tamaddon, and S. Moradi Controllable selectivity in Biginelli and Hantzsch reactions using nanoZnO as a structure base catalyst J. Mol. Catal. A Chem. 370 2013 117 122