Sulfonated Carbon Catalyzed Biginelli Reaction for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and -thiones

doi:10.1016/S1872-2067(11)60377-X

Abstract

Abstract: A sulfonated carbon material was shown to be a highly efficient, eco-friendly, and recyclable solid acid catalyst for the Biginelli reaction of β-ketoester, aldehyde, and urea or thiourea under solvent-free conditions. It gave 3,4-dihydropyrimidin-2(1H)-ones and -thiones in good to excellent yields. This method has the advantages of a simple procedure with easy work-up, short reaction time, and high yields. The catalyst can be recycled after a simple work-up and was reused four times without substantial reduction in activity.

Key words: sulfonated carbon, solid acid, Biginelli reaction, heterogeneous catalysis, solvent-free condition

Maryam MOGHADDAS, Abolghasem DAVOODNIA, Majid M. HERAVI, Niloofar TAVAKOLI-HOSEINI. Sulfonated Carbon Catalyzed Biginelli Reaction for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and -thiones[J]. Chinese Journal of Catalysis, 2012, 33(4): 706-710.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60377-X

https://www.cjcatal.com/EN/Y2012/V33/I4/706

References

1 Russowsky D, Canto R F S, Sanches S A A, D’Oca M G M, de Fatima A, Pilli R A, Kohn L K, Antonio M A, de Carvalho J E. Bioorg Chem, 2006, 34: 173
2 Kappe C O. Tetrahedron, 1993, 49: 6937
3 Rovnyak G C, Kimball S D, Beyer B, Cucinotta G, Dimarco J D, Gougoutas J, Hedberg A, Malley M, McCarthy J P. J Med Chem, 1995, 38: 119
4 Rovnyak G C, Atwal K S, Hedberg A, Kimball S D, Moreland S, Gougoutas J Z, O’Reilly B C, Schwartz J, Malley M F, Breen A L, Hertzberg R P, Johnson R K, Westley J W, Potts B C M. J Med Chem, 1992, 35: 3254
5 Sidler D R, Larsen R D, Chartrain M, Ikemoto N, Roberge C M, Taylor C S, Li W, Bills G F. PCT Int Appl WO 99 07695, 1999
6 Bruce M A, Pointdexter G S, Johnson G. PCT Int Appl WO 98 33791, 1998
7 Mayer T U, Kapoor T M, Haggarty S J, King R W, Schreiber S L, Mitchison T J. Science, 1999, 286: 971
8 Patil A D, Kumar N V, Kokke W C, Bean M F, Freyer A J, De Brosse C, Mai S, Truneh A, Faulkner D J, Carte B, Breen A L, Hertzberg R P, Johnson R K, Westley J W, Potts B C M. J Org Chem, 1995, 60: 1182
9 Snider B B, Chen J S, Patil A D, Freyer A J. Tetrahedron Lett, 1996, 37: 6977
10 Hassani Z, Islami M R, Kalantari M. Bioorg Med Chem Lett, 2006, 16: 4479
11 Tajbakhsh M, Mohajerani B, Heravi M M, Ahmadia A N. J Mol Catal A, 2005, 236: 216
12 Fu N Y, Yuan Y F, Cao Z, Wang S W, Wang J T, Peppe C. Tet-rahedron, 2002, 58: 4801
13 Kalita H R, Phukan P. Catal Commun, 2007, 8: 179
14 Chen X F, Peng Y Q. Catal Lett, 2008, 122: 310
15 Bigdeli M A, Jafari S, Mahdavinia G H, Hazarkhani H. Catal Commun, 2007, 8: 1641
16 Suzuki I, Suzumura Y, Takeda K. Tetrahedron Lett, 2006, 47: 7861
17 Heravi M M, Behbahani F K, Oskooie H A. Chin J Chem, 2008, 26: 2203
18 De S K, Gibbs R A. Synthesis, 2005: 1748
19 Reddy Ch V, Mahesh M, Raju P V K, Babu T R, Reddy V V N. Tetrahedron Lett, 2002, 43: 2657
20 Rodriguez-Dominguez J C, Bernardi D, Kirsch G. Tetrahedron Lett, 2007, 48: 5777
21 Fazaeli R, Tangestaninejad S, Aliyan H, Moghadam M. Appl Catal A, 2006, 309: 44
22 Heravi M M, Derikvand F, Bamoharramb F F. J Mol Catal A, 2005, 242: 173
23 Clark J H ed. Catalysis of Organic Reactions by Supported Reagents. New York: VCH, 1994. 35
24 Sheldon R A, Van Bekkum H eds. Catalysis Through Hetero-geneous Catalysis. Weinheim: Wiley-VCH, 2002
25 Corma A. Chem Rev, 1995, 95: 559
26 Okuhara T. Chem Rev, 2002, 102: 3641
27 Mo X H, Lotero E, Lu C Q, Liu Y J, Goodwin J G. Catal Lett, 2008, 123: 1
28 Okamura M, Takagaki A, Toda M, Kondo J N, Domen K, Tatsumi T, Hara M, Hayashi S. Chem Mater, 2006, 18: 3039
29 Shokrolahi A, Zali A, Keshavarz M H. Chin Chem Lett, 2007, 18: 1064
30 Zhou L N, Liu K, Hua W M, Yue Y H, Gao Z. Chin J Catal, 2009, 30: 196
31 Hara M, Yoshida T, Takagaki A, Takata T, Kondo J N, Hayashi S, Domen K. Angew Chem, Int Ed, 2004, 43: 2955
32 Davoodnia A, Bakavoli M, Barakouhi Gh, Tavakoli-Hoseini N. Chin Chem Lett, 2007, 18: 1483
33 Davoodnia A, Roshani M, Malaeke S H, Bakavoli M. Chin Chem Lett, 2008, 19: 525
34 Davoodnia A, Heravi M M, Rezaei-Daghigh L, Tavakoli- Hoseini N. Monatsh Chem, 2009, 140: 1499
35 Davoodnia A, Bakavoli M, Moloudi R, Khashi M, Tavakoli- Hoseini N. Chin Chem Lett, 2010, 21: 1
36 Davoodnia A, Bakavoli M, Moloudi R, Tavakoli-Hoseini N, Khashi M. Monatsh Chem, 2010, 141: 867
37 Davoodnia A, Heravi M M, Safavi-Rad Z, Tavakoli-Hoseini N. Synth Commun, 2010, 40: 2588
38 Davoodnia A, Heravi M M, Rezaei-Daghigh L, Tavakoli- Hoseini N. Chin J Chem, 2010, 28: 429
39 Davoodnia A, Allameh S, Fakhari A R, Tavakoli-Hoseini N. Chin Chem Lett, 2010, 21: 550
40 Tavakoli-Hoseini N, Davoodnia A. Asian J Chem, 2010, 22: 7197
41 Davoodnia A. Asian J Chem, 2010, 22: 1595
42 Martins M A P, Frizzo C P, Moreira D N, Buriol L, Machado P. Chem Rev, 2009, 109: 4140

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