Fe3O4 Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

doi:10.1016/S1872-2067(10)60263-X

催化学报 ›› 2011, Vol. 32 ›› Issue (9): 1484-1489.DOI: 10.1016/S1872-2067(10)60263-X

Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

Masoud NASR-ESFAHANI*, S. Jafar HOSEINI, Fatemeh MOHAMMADI

Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran

收稿日期:2011-05-22 修回日期:2011-07-13 出版日期:2011-09-09 发布日期:2015-01-24

Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

Masoud NASR-ESFAHANI*, S. Jafar HOSEINI, Fatemeh MOHAMMADI

Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran

Received:2011-05-22 Revised:2011-07-13 Online:2011-09-09 Published:2015-01-24

摘要/Abstract

摘要： The catalytic activity of Fe₃O₄ nanoparticles (NPs) in a one-pot three component condensation reaction consisting of an aromatic aldehyde, urea or thiourea, and a β-dicarbonyl under solvent-free conditions was investigated. This reaction affords the corresponding dihydropyrimidinones (thiones) in high to excellent yields. Compared with the classical Biginelli reactions this method consistently gives a high yield, easy magnetic separation, a short reaction time, and catalyst reusability.

关键词: dihydropyrimidinones, dihydropyrimidinthiones, ferroferric oxide nanoparticle, one-pot condensation, solvent-free

Abstract: The catalytic activity of Fe₃O₄ nanoparticles (NPs) in a one-pot three component condensation reaction consisting of an aromatic aldehyde, urea or thiourea, and a β-dicarbonyl under solvent-free conditions was investigated. This reaction affords the corresponding dihydropyrimidinones (thiones) in high to excellent yields. Compared with the classical Biginelli reactions this method consistently gives a high yield, easy magnetic separation, a short reaction time, and catalyst reusability.

Key words: dihydropyrimidinones, dihydropyrimidinthiones, ferroferric oxide nanoparticle, one-pot condensation, solvent-free

Masoud NASR-ESFAHANI, S. Jafar HOSEINI, Fatemeh MOHAMMADI. Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions[J]. 催化学报, 2011, 32(9): 1484-1489.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(10)60263-X

https://www.cjcatal.com/CN/Y2011/V32/I9/1484

参考文献

1Tanaka K, Toda F. Chem Rev, 2000, 100: 1025
2Cave G W V, Raston C L, Scott J L. Chem Commun, 2001: 2159
3Rovnyak G C, Kimball S D, Beyer B, Cucinotta G, Dimarco J D, Gougoutas J, Hedberg A, Malley M, McCarthy J P, Zhang R, Moreland S. J Med Chem, 1995, 38: 119
4Kappe C O, Fabian W M F, Semones M A. Tetrahedron, 1997, 53: 2803
5Atwal K S, Swanson B N, Unger S E, Floyd D M, Moreland S, Hedberg A, O’Reilly B C. J Med Chem, 1991, 34: 806
6Grover G J, Dzwonczyk S, McMullen D M, Normadin D E, Parham S G, Sleph P G, Moreland S. J Cardiovasc Pharmacol, 1995, 26: 289
7Gartner M, Sunder-Plassmann N, Seiler J, Utz M, Vernos I, Surrey T, Giannis A. ChemBioChem, 2005, 6: 1173
8Kappe C O, Shishkin O V, Uray G, Verdino P. Tetrahedron, 2000, 56: 1859
9Mitra A K, Banerjee K. Synlett, 2003, 1509
10Biginelli P. Gazz Chim Ital, 1893, 23: 360
11Atwal K S, Rovnyak G C, O’Reilly B C, Schwartz J. J Org Chem, 1989, 54: 5898
12O’ Reilly B C, Atwal K S. Heterocycles, 1987, 26: 1185
13Kappe C O. Tetrahedron, 1993, 49: 6937
14Hu E H, Sidler D R, Dolling U H. J Org Chem, 1998, 63: 3454
15Khodaei M M, Khosropour A R, Beygzadeh M. Synth Com-mun, 2004, 34: 1551
16Huang Y, Yang F, Zhu C. J Am Chem Soc, 2005, 127: 16386
17Wang S, Wang Z, Zha Z. Dalton Trans, 2009: 9363
18Firouzabadi H, Iranpoor N, Ghaderi A, Ghavami M, Hoseini S J. Bull Chem Soc Jpn, 2011, 84: 100
19Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J M. Chem Rev, 2011, 111: 3036
20Firouzabadi H, Iranpoor N, Gholinejad M, Hoseini S J. Adv Synth Catal, 2011, 353: 125
21Nasr-Esfahani M, Karami B, Montazerozohori M, Abdi K. J Heterocycl Chem, 2008, 45: 1183
22Nasr-Esfahani M, Khosropour A R. Bull Korean Chem Soc, 2005, 26: 1331
23Kang Y S, Rishbud S, Rabolt J F, Stroeve P. Chem Mater, 1996, 8: 2209
24Park J, An K, Hwang Y, Park J G, Noh H J, Kim J Y, Park J H, Hwang N M, Hyeon T. Nature Mater, 2004, 3: 891
25Khabazzadeh H, Saidi K, Sheibani H. Bioorg Med Chem Lett, 2008, 18: 278
26Yu Y, Liu D, Liu C, Luo G. Bioorg Med Chem Lett, 2007, 17: 3508
27Ramalingan C, Kwak Y -W. Tetrahedron, 2008, 64: 5023
28Rodríguez-omínguez J C, Bernardi D, Kirsch G. Tetrahedron Lett, 2007, 48: 5777
29Salehi P, Dabiri M, Zolfigol M A, Bodagh Fard M A. Tetrahe-dron Lett, 2003, 44: 2889
30Varala R, Alam M M, Adapa S R. Synlett, 2003: 67
31Reddy K R, Reddy C V, Mahesh M, Raju P V K, Reddy V V N. Tetrahedron Lett, 2003, 44: 8173
32Litvic M, Vecenaj I, Ladisic Z M, Lovric M, Vinkovic V, Filipan-Litvic M. Tetrahedron, 2010, 66: 3463
33Bose D S, Kumar R K, Fatima L. Synlett, 2004: 279

[1]	Abdol R. Hajipour, Hirbod Karimi, Afshin Koohi. Selective oxidation of alcohols over nickel zirconium phosphate[J]. 催化学报, 2015, 36(7): 1109-1116.
[2]	Nader Ghaffari Khaligh, Sharifah Bee Abd Hamid. 4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for the synthesis of pyrano[4, 3-b]pyran derivatives using thermal and ultrasonic irradiation[J]. 催化学报, 2015, 36(5): 728-733.
[3]	Hossein Naeimi, Hossein Foroughi. Efficient, environmentally benign, one-pot procedure for the synthesis of 1, 5-benzodiazepine derivatives using N-methyl-2-pyrrolidonium hydrogen sulphate as an ionic liquid catalyst under solvent-free conditions[J]. 催化学报, 2015, 36(5): 734-741.
[4]	Abdol R. Hajipour, Hirbod Karimi, Amir Masti. Acetylation of alcohols and phenols under solvent-free conditions using iron zirconium phosphate[J]. 催化学报, 2015, 36(4): 595-602.
[5]	Nader Ghaffari Khaligh. One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1’-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst[J]. 催化学报, 2014, 35(9): 1497-1503.
[6]	Bahador Karami, Mahtab Kiani, Mohsen Ahmad Hoseini. In(OTf)₃ as a powerful and recyclable catalyst for Pechmann condensation without solvent[J]. 催化学报, 2014, 35(7): 1206-1211.
[7]	Nader Ghaffari Khaligh, Parisa Ghods Ghasem-Abadi. N-Sulfonic acid poly(4-vinylpyridinum) hydrogen sulfate as a novel, efficient, and reusable solid acid catalyst for acylation under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1126-1135.
[8]	Nader Ghaffari Khaligh. Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst[J]. 催化学报, 2014, 35(7): 1036-1042.
[9]	Arash Ghorbani-Choghamarani, Shima Rashidimoghadam. One-pot synthesis of 1-amidoalkyl-2-naphthols catalyzed by melamine-Br₃ under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1024-1029.
[10]	Abolghasem Davoodnia, Maryam Khashi, Niloofar Tavakoli-Hoseini. Cerium (IV) sulfate：A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions[J]. 催化学报, 2014, 35(7): 1054-1058.
[11]	Abolghasem Davoodnia, Rahil Mahjoobin, Niloofar Tavakoli-Hoseini. A facile, green, one-pot synthesis of amidoalkyl naphthols under solvent-free conditions catalyzed by a carbon-based solid acid[J]. 催化学报, 2014, 35(4): 490-495.
[12]	Nader Ghaffari Khaligh. Three-component, one-pot synthesis of benzo[f]indenoquinoline derivatives catalyzed by poly(4-vinylpyridinium) hydrogen sulfate[J]. 催化学报, 2014, 35(4): 474-480.
[13]	Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Omid Khaledian, Vahid Khakyzadeh. Condensation of 2-naphtol with arylaldehydes using acetic acid functionalized ionic liquids as highly efficient and reusable catalysts[J]. 催化学报, 2014, 35(4): 573-578.
[14]	Ali Keivanloo, Mahdi Mirzaee, Mohammad Bakherad, Atena Soozani. Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions[J]. 催化学报, 2014, 35(3): 362-367.
[15]	Saeed Farhadi, Kosar Jahanara. ZnAl₂O₄@SiO₂ nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions[J]. 催化学报, 2014, 35(3): 368-375.

Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

Fe₃O₄ Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics