One-Pot and Green Procedure for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones Using ZnO Nanoparticles as a Solid Acid Catalyst
2
조회
0
다운로드
0
인용
0
참고문헌
키워드
초록
A convenient and efficient method has been developed for the one-pot synthesis of dihydropyrimidinones (DHPMs) compounds. Dihydropyrimidinone derivatives were synthesized in good yields using ethyl acetoacetate, aldehyde (aromatic and aliphatic) and urea or thiourea in the presence of ZnO nanoparticles as a catalyst in H2O as solvent at 80 oC. This green chemistry procedure applied to the Biginelli reaction using ZnO nanoparticles as catalyst and illustrated as a rapid preparation of DHPMs in water as solvent. The products were identified by physical data (mp) by comparison with those reported in the literatures.
Abstract
A convenient and efficient method has been developed for the one-pot synthesis of dihydropyrimidinones (DHPMs) compounds. Dihydropyrimidinone derivatives were synthesized in good yields using ethyl acetoacetate, aldehyde (aromatic and aliphatic) and urea or thiourea in the presence of ZnO nanoparticles as a catalyst in H2O as solvent at 80 oC. This green chemistry procedure applied to the Biginelli reaction using ZnO nanoparticles as catalyst and illustrated as a rapid preparation of DHPMs in water as solvent. The products were identified by physical data (mp) by comparison with those reported in the literatures.
참고문헌 (52)
- Domling, A, , Chem. Rev, 106, pp.17~ (2006)
- Akritopoulou- Zanze, I, , Heterocycles, 73, pp.125~ (2007)
- Akritopoulou-Zanze, I, , Curr. Opinion Chem. Biol, 12, pp.324~ (2008)
- Hulme, C, "Multicomponent Reactions", pp.311~ (2005), Wiley-VCH, Verlag GmbH & Co. KgaA
- Hulme, C, , Current Med. Chem, 10, pp.51~ (2003)
- Marcaccini, S, "Multicomponent Reactions", pp.33~ (2005), Wiley-VCH, Verlag GmbH & Co. KgaA
- Jieping Zhu, , Eur. J. Org. Chem, pp.1133~ (2003)
- Nair, V, , Acc. Chem. Res, 36, pp.899~ (2003)
- Domling, A, , Angew. Chem., Int. Ed, 39, pp.3168~ (2000)
- Ganem, B, , Acc. Chem. Res, 42, pp.463~ (2009)
- Biginelli, P, , Gazz. chim. Ital, 23, pp.360~ (1893)
- Patil, A. D, , J. Org. Chem, 60, pp.1182~ (1995)
- Snider, B. B, , Tetrahedron Lett, 37, pp.6977~ (1996)
- Heys, L, , J. Chem. Soc. Rev, 29, pp.57~ (2000)
- Tu, S, , Tetrahedron Lett, 44, pp.6153~ (2003)
- Hu, E. H, , J. Org. Chem, 63, pp.3454~ (1998)
- Ranu, B. C, , J. Org. Chem, 65, pp.6270~ (2000)
- Ramalinga, K, , Synlett, pp.863~ (2001)
- Yadav, J. S, , Synthesis, pp.1341~ (2001)
- Reddy, V, , Tetrahedron Lett, 43, pp.2657~ (2002)
- Fu, N. Y, , Tetrahedron, 58, pp.4801~ (2002)
- Fan, X, , J. Chem. Res, pp.436~ (2002)
- Lu, J, , Synthesis, pp.466~ (2002)
- Varela, R, , Synlett, 67 (2003)
- Bose, D. S, , J. Org. Chem, 68, pp.587~ (2003)
- Sabitha, S, , Synlett, pp.858~ (2003)
- Paraskar, A. S, , Tetrahedron Lett, 44, pp.3305~ (2003)
- Yadav, J. S, , J. Chem. Res, pp.354~ (2000)
- Dondoni, A, , Tetrahedron Lett, 42, pp.7975~ (2001)
- Stadler, A, , J. Chem. Soc. Perkin Trans, 1, pp.1363~ (2000)
- Kappe, C. O, , Synthesis, pp.1799~ (1999)
- Kidwai, M, , J. Chem. Soc. Perkin Trans, 1, pp.1845~ (2002)
- Maiti, G, , Tetrahedron Lett, 44, pp.2757~ (2003)
- Baruah, P. P, , Chem. Lett, 10, pp.1038~ (2002)
- Reddy, K. R, , Tetrahedron Lett, 44, pp.8173~ (2003)
- Bigi, F, , Tetrahedron Lett, 40, pp.3465~ (1999)
- Dondoni, A, , Tetrahedron Lett, 42, pp.7975~ (2001)
- Wipf, P, , Tetrahedron Lett, 36, pp.7819~ (1995)
- Salehi, P, , Tetrahedron Lett, 44, pp.2889~ (2003)
- Yadav, J. S, , J. Chem. Soc. Perkin Trans, 1, pp.1939~ (2001)
- Mitra, A. K, , Synlett, 10, pp.1509~ (2003)
- Tamaddon, F, , J. Mol. Catal. A: Chem, 370, pp.117~ (2013)
- Tamaddon, F, , Tetrahedron Lett, 46, pp.7841~ (2005)
- Tamaddon, F, , J. Mol. Catal. A: Chem, 351, pp.41~ (2011)
- Tamaddon, F, , Catal. Commun, 12, pp.1477~ (2011)
- Tamaddon, F, , J. Mol. Catal. A: Chem, 337, pp.52~ (2011)
- Tamaddon, F, , Tetrahedron Lett, 51, pp.1187~ (2010)
- Ghosh, R, , J. Mol. Catal. A: Chem, 217, pp.47~ (2004)
- Gholap, A. R, , Green Chem, 6, pp.147~ (2004)
- Liu, C, , J. Mol. Catal. A: Chem, 258, pp.367~ (2006)
- Reddy, C. V, , Tetrahedron Lett, 43, pp.2657~ (2002)
- Kappe, C. O, , Molecules, 3, pp.1~ (1998)