Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions

doi:10.1016/S1872-2067(12)60759-1

催化学报 ›› 2014, Vol. 35 ›› Issue (3): 362-367.DOI: 10.1016/S1872-2067(12)60759-1

Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions

Ali Keivanloo, Mahdi Mirzaee, Mohammad Bakherad, Atena Soozani

School of Chemistry, Shahrood University of Technology, Shahrood, Iran

收稿日期:2013-08-22 修回日期:2013-11-25 出版日期:2014-02-26 发布日期:2014-02-26
通讯作者: Ali Keivanloo

Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions

Ali Keivanloo, Mahdi Mirzaee, Mohammad Bakherad, Atena Soozani

School of Chemistry, Shahrood University of Technology, Shahrood, Iran

Received:2013-08-22 Revised:2013-11-25 Online:2014-02-26 Published:2014-02-26
Contact: Ali Keivanloo

摘要/Abstract

摘要：

A simple, green, and efficient synthesis protocol for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using boehmite nanoparticles as catalyst was developed. It did not use any toxic metal catalysts or corrosive acidic reagents. The method gave good to excellent yields and has short reaction time, operational simplicity, and a recyclable catalyst.

关键词: Boehmite nanoparticle, One-pot synthesis, Multicomponent synthesis, Dihydropyrimidine, Solvent-free

Abstract:

Key words: Boehmite nanoparticle, One-pot synthesis, Multicomponent synthesis, Dihydropyrimidine, Solvent-free

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.

×
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(12)60759-1

https://www.cjcatal.com/CN/Y2014/V35/I3/362

参考文献

[1] Cariou C C A, Clarkson G J, Shipman M. J Org Chem, 2008, 73: 9762
[2] Zhou L, Bohle D S, Jiang H F, Li C J. Synlett, 2009: 937
[3] Mukhopadhyay C, Tapaswi P K, Drew M G B. Tetrahedron Lett, 2010, 51: 3944
[4] Bonfield E R, Li C J. Adv Synth Catal, 2008, 350: 370
[5] Zhu J P. Eur J Org Chem, 2003: 1133
[6] Chapman C J, Frost C G. Synthesis, 2007: 1
[7] Wang L M, Sheng J, Zhang L, Han J W, Fan Z Y, Tian H, Qian C T. Tetrahedron, 2005, 61: 1539
[8] Atwal 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
[9] Rovnyak 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
[10] Atwal K S, Rovnyak G C, Kimball S D, Floyd D M, Moreland S, Swanson B N, Gougoutas J Z, Schwartz J, Smillie K M, Malley M F. J Med Chem, 1990, 33: 2629
[11] Kappe C O, Shishkin O V, Uray G, Verdino P. Tetrahedron, 2000, 56: 1859
[12] Kappe C O. Eur J Med Chem, 2000, 35: 1043
[13] Butters M, Davies C D, Elliott M C, Hill-Cousins J, Kariuki B M, Doi L L, Wood J L, Wordingham S V. Org BiomolChem, 2009, 7: 5001
[14] Heys L, Moore C G, Murphy P. J Chem Soc Rev, 2000, 29: 57
[15] Biginelli P. Gazz Chim Ital, 1893, 23: 360
[16] Lu J, Bai Y J. Synthesis, 2002: 4660
[17] Fesenko A A, Solovyev P A, Shutalev A D. Tetrahedron, 2010, 66: 940
[18] Tamaddon F, Razmi Z, Jafari A A. Tetrahedron Lett, 2010, 51: 1187
[19] Shen Z L, Xu X P, Ji S J. J Org Chem, 2010, 75: 1162
[20] Singh K, Singh S. Tetrahedron, 2009, 65: 4106
[21] Suzuki I, Iwata Y, Takeda K. Tetrahedron Lett, 2008, 49: 3238
[22] Schmidt R J, Lombardo L J, Traeger S C, Williams D K. Tetrahedron Lett, 2008, 49: 3009
[23] Fu N Y, Yuan Y F, Cao Z, Wang S W, Wang J T, Peppe C. Tetrahedron, 2002, 58: 4801
[24] Hu E H, Slider D R, Dolling U H. J Org Chem, 1998, 63: 3454
[25] Khabazzadeh H, Saidi K, Sheibani H. Bioorg Med Chem Lett, 2008, 18: 278
[26] Varala R, Alam M M, Adapa S R. Synlett, 2003: 67
[27] Paraskar A S, Dewkar G K, Sudalai A. Tetrahedron Lett, 2003, 44: 3305
[28] Ma Y, Qian C T, Wang L M, Yang M. J Org Chem, 2000, 65: 3864
[29] Yadav J S, Reddy B V S, Srinivas R, Venugopal C, Ramalingam T. Synthesis, 2001: 1341
[30] Li N, Chen X H, Song J, Luo S W, Fan W, Gong L Z. J Am Chem Soc, 2009, 131: 15301
[31] Chen X H, Xu X Y, Liu H, Cun L F, Gong L Z. J Am Chem Soc, 2006, 128: 14802
[32] Amini M M, Mirzaee M. J Sol-Gel Sci Technol, 2005, 36: 19
[33] Mirzaee M, Amini M M, Sadeghi M, Mousavi F Y, Sharbatdaran M. Ceram Silikaty, 2005, 49: 40
[34] Kharat A N, Mirzaee M, Amini M M. Asian J Chem, 2008, 20: 915
[35] Keivanloo A, Bakherad M, Nasr-Isfahani H, Esmaily S. Tetrahedron Lett, 2012, 53: 3126
[36] Bakherad M, Keivanloo A, Jajarmi S. Tetrahedron, 2012, 68: 2107
[37] Keivanloo A, Bakherad M, Rahimi A. Synthesis, 2010: 1599
[38] Bakherad M, Nasr-Isfahani H, Keivanloo A, Doostmohammadi N. Tetrahedron Lett, 2008, 49: 3819
[39] Bakherad M, Keivanloo A, Samangooei S. Tetrahedron Lett, 2012, 53: 5773
[40] Keivanloo A, Bakherad M, Bahramian B, Rahmani M, Taheri S A N. Synthesis, 2011: 325
[41] Keivanloo A, Bakherad M, Bahramian B, Baratnia S. Tetrahedron Lett, 2011, 52: 1498
[42] Bakherad M, Keivanloo A, Bahramian B, Jajarmi S. Appl Catal A, 2010, 390: 135
[43] Ramu E, Kotra V, Bansal N, Varala R, Adapa S R. Rasayan J Chem, 2008, 1: 188
[44] Karade H N, Sathe M, Kaushik M P. Molecules, 2007, 12: 1341
[45] Maradur S P, Gokavi G S. Catal Commun, 2007, 8: 279
[46] Chitra S, Pandiarajan K. Tetrahedron Lett, 2009, 50: 2222
[47] Bigdeli M A, Jafari S, Mahdavinia G H, Hazarkhani H. Catal Commun, 2007, 8: 1641
[48] Shaterian H R, Hosseinian A, Ghashang M, Khorami F, Karimpoor N. Phosphorous Sulfur Silicon Relat Elem, 2009, 184: 2333
[49] Zumpe F L, Fluess M, Schmitz K, Lender A. Tetrahedron Lett, 2007, 48: 1421
[50] Rodriguez-Dominguez J C, Bernardi D, Kirsch G. Tetrahedron Lett, 2007, 48: 5777
[51] Shete D K, Surve S S, Patil S B, Narade S B, Patil K S, Pore Y V. Der Pharmacia Lettre, 2010, 2(3): 59
[52] Sangshetti J N, Kokare N D, Shinde D B. J Heterocycl Chem, 2008, 45: 1191
[53] Chitra S, Devanathan D. Arch Appl Sci Res, 2012, 4: 1716

Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions

Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones 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

[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]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[13]	Fahime Khorami, Hamid Reza Shaterian. Silica-bonded propylpiperazine-N-sulfamic acid as recyclable solid acid catalyst for preparation of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromenes and hydroxy-substituted naphthalene-1,4-dione derivatives[J]. 催化学报, 2014, 35(2): 242-246.
[14]	Abdol R. Hajipour, Hirbod Karimi. Acetylation of alcohols and phenols under solvent-free conditions using copper zirconium phosphate[J]. 催化学报, 2014, 35(12): 1982-1989.
[15]	Ahmad Nakhaei, Abolghasem Davoodnia. Application of a Keplerate type giant nanoporous isopolyoxomolybdate as a reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles[J]. 催化学报, 2014, 35(10): 1761-1767.