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

doi:10.1016/S1872-2067(14)60041-3

Abstract

Abstract:

Cerium (IV) sulfate tetrahydrate, Ce(SO₄)₂·4H₂O, is a novel inorganic solid acidic catalyst that efficiently catalyzes the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via the one-pot three-component reaction of isatoic anhydride, aromatic aldehydes, and a nitrogen source (ammonium acetate, ammonium carbonate, ammonium chloride, or methylamine) under solvent-free conditions. The desired products are obtained in short reaction time with high yields. The catalyst is inexpensive and readily available and can be recovered conveniently and reused such that considerable catalytic activity can still be achieved after the fifth run. Easy work-up and avoiding the use of harmful organic solvents are other advantages of this simple procedure.

Key words: Cerium (IV) sulfate, 2,3-Dihydroquinazolin-4(1H)-ones, Heterogeneous catalysis, Solvent-free conditions

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]. Chinese Journal of Catalysis, 2014, 35(7): 1054-1058.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60041-3

https://www.cjcatal.com/EN/Y2014/V35/I7/1054

References

[1] Dömling A. Chem Rev, 2006, 106: 17
[2] Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
[3] Davoodnia A, Khojastehnezhad A. J Chil Chem Soc, 2012, 57: 1385
[4] Sadanadam Y S, Reddy K R M, Rao A B. Eur J Med Chem, 1987, 22: 169
[5] Hour M J, Huang L J, Kuo S C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K H. J Med Chem, 2000, 43: 4479
[6] Davoodnia A, Allameh S, Fakhari A R, Tavakoli-Hoseini N. Chin Chem Lett, 2010, 21: 550
[7] Chen J X, Wu H Y, Su W K. Chin Chem Lett, 2007, 18: 536
[8] Yassaghi G, Davoodnia A, Allameh S, Zare-Bidaki A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2012, 33: 2724
[9] Wang J K, Zong Y X, Fu R G, Niu Y Y, Yue G R, Quan Z G, Wang X C, Pan Y. Ultrason Sonochem, 2014, 21: 29
[10] Li S W, Nair M G, Edwards D M, Kisliuk R L, Gaumont Y, Dev I K, Duch D S, Hmphrys J, Smith G K, Ferone R. J Med Chem, 1991, 34: 2746
[11] Moore J A, Sutherland G J, Sowerby R, Kelly E G, Palermo S, Webster W. J Org Chem, 1969, 34: 887
[12] Yale H L. J Heterocycl Chem, 1977, 14: 1357
[13] Darvatkar N B, Bhilare S V, Deorukhkar A R, Raut D G, Salunkhe M M. Green Chem Lett Rev, 2010, 3: 301
[14] Dabiri M, Salehi P, Baghbanzadeh M, Zolfigol M A, Agheb M, Heydari S. Catal Commun, 2008, 9: 785
[15] Saffar-Teluri A, Bolouk S. Monatsh Chem, 2010, 141: 1113
[16] Khaksar S, Mohammadzadeh Talesh S. C R Chim, 2012, 15: 779
[17] Chen Y J, Shan W G, Lei M, Hu L H. Tetrahedron Lett, 2012, 53: 5923
[18] Safari J, Gandomi-Ravandi S. J Mol Catal A, 2013, 371: 135
[19] Song Z G, Liu L L, Wang Y, Sun X H. Res Chem Intermed, 2012, 38: 1091
[20] Salehi P, Dabiri M, Baghbanzadeh M, Bahramnejad M. Synth Commun, 2006, 36: 2287
[21] Niknam K, Mohammadizadeh M R, Mirzaee S. Chin J Chem, 2011, 29: 1417
[22] Karimi-Jaberi Z, Arjmandi R. Monatsh Chem, 2011, 142: 631
[23] Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi A A. Tetrahedron Lett, 2005, 46: 6123
[24] Niknam K, Jafarpour N, Niknam E. Chin Chem Lett, 2011, 22: 69
[25] Zhang Z H, Lu H Y, Yang S H, Gao J W. J Comb Chem, 2010, 12: 643
[26] Horiuchi C A, Fukushima T, Furuta N, Chai W, Ji S J, Saito Y, Hashimoto C, Takahashi T T, Sugiyama T, Muto A, Sakata Y, Nozaki S. J Chem Res (R), 2003: 270
[27] Selvam N P, Perumal P T. Tetrahedron Lett, 2006, 47: 7481
[28] He L Y, Horiuchi C A. Appl Organometal Chem, 1999, 13: 867
[29] Itoh K, Takahashi S, Ueki T, Sugiyama T, Takahashi T T, Horiuchi C A. Tetrahedron Lett, 2002, 43: 7035
[30] Ko S, Yao C F. Tetrahedron, 2006, 62: 7293
[31] Davoodnia A, Zare-Bidaki A, Behmadi H. Chin J Catal (催化学报), 2012, 33: 1797
[32] Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
[33] Davoodnia A, Khojastehnezhad A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2243
[34] Mohammadzadeh-Dehsorkh N, Davoodnia A, Tavakoli-Hoseini N, Moghaddas M. Synth React Inorg Met-Org Nano-Met Chem, 2011, 41: 1135
[35] Emrani A, Davoodnia A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2385
[36] Davoodnia A, Khashi M, Tavakoli-Hoseini N. Chin J Catal (催化学报), 2013, 34: 1173
[37] Khojastehnezhad A, Davoodnia A, Bakavoli M, Tavakoli-Hoseini N, Zeinali-Dastmalbaf M. Chin J Chem, 2011, 29: 297
[38] Seifi N, Zahedi-Niaki M H, Reza Barzegari M, Davoodnia A, Zhiani R, Kaju A A. J Mol Catal A, 2006, 260: 77
[39] Taghavi-Khorasani F, Davoodnia A. Res Chem Intermed, in press, doi: 10.1007/s11164-013-1356-0
[40] Saburi E, Davoodnia A, Tavakoli-Hoseini N. Synth React Inorg Met-Org Nano-Met Chem, 2011, 41: 1063