Note
Magnesium Bromide and Magnesium Chloride Hexahydrate Catalyzed One-Pot Synthesis of Dihydropyrimidines via Biginelli Reaction under Solvent-Free Conditions
Şirin Gülten,
Corresponding Author
Şirin Gülten
Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, Çanakkale 17020 Turkey
E-mail: [email protected]Search for more papers by this authorŞirin Gülten,
Corresponding Author
Şirin Gülten
Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, Çanakkale 17020 Turkey
E-mail: [email protected]Search for more papers by this authorAbstract
Biologically important 12 new important 3,4-dihydropyrimidin-2-(1H)-ones (-thiones) were synthesized with in one-pot three-component Biginelli reaction from the corresponding aromatic aldehydes (5-methyl-2-thiophenecarboxaldehyde and 2-chloro-5-nitrobenzaldehyde), β-keto esters (ethylacetoacetate, allylacetoacetate, and t-butylacetoacetate), and urea/thiourea in the presence of catalytic amount of magnesium bromide and magnesium chloride hexahydrate as nontoxic, inexpensive, and easily available catalysts under solvent-free conditions at 80 and 100°C. Compared with the catalyst-free three-component Biginelli reaction conditions, this method consistently has the advantage of short reaction time (45–100 min) and good to excellent yields (75–91%).
REFERENCES AND NOTES
- 1 Baldwin, J. J.; Pitzenberger, S. M.; McClure, D. E. U.S. Patent 4675321,1988.
- 2 Kastron, V.V.; Vitrolin, R. O.; Khanina, E. L.; Dubur, G. Y.; Kimenis, A. A.; Kondratenko, N. V.; Popov, V. I.; Yagupolsky, L. M.; Kolomeitsev, A. A. U.S. Patent4738965,1988.
- 3 Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. F. J Med Chem 1990, 33, 1510.
- 4 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.
- 5 Ertan, M.; Balkan, A.; Saraç, S.; Uma, S.; Renaud. J. F.; Rollad, Y. Arch Pharm 1991, 324, 135.
- 6 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.
- 7 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. J Med Chem 1992, 35, 3254.
- 8 Kappe, C. O. Tetrahedron 1993, 49, 6937.
- 9 Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; Mcarthy, J. P.; Zhang, R.; Moreland, S. J. J Med Chem 1995, 38, 119.
- 10 Grover, G. J.; Dzwonczyk, S.; McMullen, D. M.; Normandin, D. E.; Parham, C. S.; Sleph, P. G.; Moreland, S. J Cardiovasc Pharmacol 1995, 26, 289.
- 11 Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
- 12 Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971.
- 13 Barrow, J. C.; Nantermet, P. G.; Nagarathnam, D.; Forray, C. J Med Chem 2000, 43, 2703.
- 14 Kappe, C. O. Acc Chem Res 2000, 33, 879.
- 15 Kappe, C. O. Eur. J Med Chem 2000, 35, 1043.
- 16 Kappe, C. O.; Shishkin, O. V.; Uray, G.; Verdino, P. Tetrahedron 2000, 56, 1859.
- 17 Brands, M.; Endermann, R.; Gahlmann, R.; Krüger, J.; Raddatz, S. Bioorg Med Chem Lett 2003, 13, 241.
- 18 Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem Rev 2003, 103, 893.
- 19 Kappe, C. O. QSAR Comb Sci 2003, 22, 630.
- 20 Yarim, M.; Saraç, S.; Kilic, F. S.; Erol, K. II Farmaco 2003, 58, 17.
- 21 Bahekar, S. S.; Shinde, D. B. Bioorg. Med Chem Lett 2004, 14, 1733.
- 22 Kappe, C. O. The Biginelli reaction. Multicomponent reactions. J. Zhu; H. Bienaymé, Eds.; Wiley-VCH, Weinheim, 2005; p 95.
- 23 Zorkun, I. S.; Saraç, S.; Çelebi, S.; Erol, K. Bioorg Med Chem 2006, 14, 8582.
- 24 Sujatha, K.; Shanmugam, P.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. Bioorg Med Chem Lett 2006, 16, 4893.
- 25 Ashok, M.; Holla, B. S.; Kumari, N. S. Eur J Med Chem 2007, 42, 380.
- 26 Saraç, S.; Çiftçi, M.; Zorkun, I. S.; Tunç, O.; Erol, K. Arzneim-Forsch/Drug Res 2007, 57, 137.
- 27 Singh, K.; Arora, D.; Falkowski, D.; Liu, Q.; Moreland, R. Eur J Org Chem 2009, 19, 3258.
- 28 Kolosov, M. A.; Orlov, V. D.; Beloborodov, D. A; Dotsenko, V. V. Mol Divers 2009, 13, 5.
- 29 Snider, B. B.; Shi, Z. J Org Chem 1993, 58, 3828.
- 30 Heys, L.; Moore, C. G.; Murphy, P. J Chem Soc Rev 2000, 29, 57.
- 31 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.
- 32 Rama Rao, A. V.; Gurjar, M. K.; Vasudevan, J. J Chem Soc Chem Commun 1995, 1369.
- 33 Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. Tetrahedron Lett 1996, 37, 6977.
- 34 Kapoor, T. M.; Mayer, T. M.; Coughlin, M. L.; Mitchison, T. J. J Cell Biol 2000, 150, 975.
- 35 Haggarty, S. J.; Mayer, T. M.; Miyamoto, D. T.; Fathi, R.; King, R. W.; Mitchison, T. J.; Schreiber, S. L. Chem Biol 2000, 7, 275.
- 36 Lu, J.; Bai, Y. Synthesis 2002, 466.
- 37 Wang, Z. T.; Xu, L. W.; Xia, C. G.; Wang, H. Q. Tetrahedron Lett 2004, 45, 7951.
- 38 Bahekar, S. S.; Kotharkar, S. A.; Shinde, D. B. Mendeleev Commun 2004, 14, 210.
- 39 Bose, D. S.; Sudharshan, M.; Chavhan, S. W. ARKIVOC 2005,( iii),228.
- 40 Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. J Mol Catal A: Chem 2005, 242, 173.
- 41 Cepanec, I.; Litvić, M.; Bartolinčić, A.; Lovrić, M. Tetrahedron Lett 2005, 61, 4275.
- 42 Ostras, K. S.; Gorobets, N. K.; Desenko, S. M.; Musatov, V. I. Mol Divers 2006, 10, 483.
- 43 Fazaeli, R.; Tangestaninejad, S.; Aliyan, H.; Moghadam, M. Appl Catal A: Gen 2006, 309, 44.
- 44 Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. Appl Catal A: Gen 2006, 300, 85.
- 45 Ahmed, N.; van Lier, J. E. Tetrahedron Lett 2007, 48, 5407.
- 46 Shaabani, A.; Maleki, A. Chem Pap 2007, 61, 333.
- 47 Adibi, H.; Samimi, H. A.; Beygzadeh, M. Catal Commun 2007, 8, 2119.
- 48 Rodríguez-Domínquez, J. C.; Bernardi, D.; Kirsch, G. Tetrahedron Lett 2007, 48, 5777.
- 49 Chen, X.; Peng, Y. Catal Lett 2008, 122, 310.
- 50 Khaleghi, S.; Heravi, M. M.; Khosroshahi, M.; Behbahani, F, K.; Daroogheha, Z. Green Chem Lett Rev 2008, 1, 133.
- 51 Jain, S. L.; Prasad, V. V. D. N.; Sain, B. Catal Commun 2008, 9, 499.
- 52 Boumoud, T.; Boumoud, B.; Rhouati, S.; Belfaitah, A.; Debache, A.; Mosset, P. Acta Chim Slov 2008, 55, 617.
- 53 Quan, Z. J.; Da, Y. X.; Zhang, Z.; Wang, X. C. Catal Commun 2009, 10, 1146.
- 54 Kashima, C.; Takahashi, K.; Fukusaka, K. J. J Heterocycl Chem 1995, 32, 1775.
- 55 Kim, D. Y.; Lee, Y. M.; Choi, Y. J. Tetrahedron 1999, 55, 12983.
- 56 Jui, W. H.; Chair, D. C.; Man, K. L. Tetrahedron Lett 1999, 40, 8647.
- 57 Matsumoto, A.; Nakamura, S. J. Appl. Polym. Sci 1999, 74, 290.
- 58 Kashima, C.; Fukusaka, K.; Takahashi, K.; Yokoyama, Y. J Org Chem 1999, 64, 1108.
- 59 Pansare, S. V.; Malusare, M. G.; Rai, A. N. Synth Commun 2000, 30, 2587.
- 60 Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org Lett 2002, 4, 1127.
- 61 Salehi, H.; Guo, Q. X. Synth Commun 2004, 34, 171.
- 62 Salehi, H.; Guo, Q. X. Chin J Chem 2005, 23, 91.
- 63 Salehi, H.; Li, Q. R.; Guo, Q. X. Chin. J Chem Phys 2006, 19, 84.
- 64 Zhang, G. L.; Cai, X. H. Synth Commun 2004, 35, 829.
- 65 Ranu, B. C.; Hajra, A.; Dey, S. S. Org Proc Res Dev 2002, 6, 817.
