Molybdenum Oxide Supported on Silica (MoO /SiO ): An Efficient and Reusable Catalyst for the Synthesis of 1,8-dioxodecahydroacridines Under Solvent-free Conditions
DOI:
https://doi.org/10.29356/jmcs.v59i1.11Keywords:
Silica supported molybdenum oxide, multicomponent reaction, solvent-free conditions, 1, 8-dioxodecahydroacridines.Abstract
Silica supported molybdenum oxide (MoO3/SiO2) was found to be an efficient, eco-friendly and heterogeneous catalyst for the multicomponent reaction of aromatic aldehydes, dimedone and ammonium acetate or aromatic amines under solvent-free conditions to afford the corresponding 1,8-dioxodecahydroacridines in high yields. The catalyst can be easily recovered and reused for several times without considerable loss of activity. Furthermore, the present method offers several advantages, such as an easy experimental and work-up procedures, short reaction times and good to excellent yields.Downloads
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Zhu, J.; Bienayme, H. in: Multicomponent Reactions, Wiley Weinheim, 2005, 169-198.
Spalding, D. P.; Chapin, E. C.; Mosher, H. S. J. Org. Chem. 1954, 19, 357.
Gamega, S. A.; Spicer, J. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Deny, W. A. J. Med. Chem. 1999, 42, 2383.
Antonini, I.; Polucci, P.; Kelland, L. R.; Menta, E.; Pescalli, N.; Martelli, S. J. Med. Chem. 1999, 42, 2535.
Ngadi, L.; Galy, A. M.; Galy, J. P.; Barbe, J.; Cremieux, A.; Chevalier, J.; Sharples, D. Eur.J. Med. Chem. 1990, 25, 67.
Berkan, O.; Sarac, B.; Simsek, R.; Yildirim, S.; Sariogli, Y.; Safak, C. Eur. J. Med. Chem. 2002, 37, 519.
(a) Khurana, J. M.; Maikap, G. C.; Mehta, S. Synthesis 1990, 731. (b) Matsumoto, H.; Arai, T.; Takahashi, M.; Ashizawa, T.; Nakano, T.; Nagai, Y. Bull. Chem. Soc. Jpn. 1983, 56, 3009. (c) Nakano, T.; Takahashi, M.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613.
Murugan, P.; Shanmugasundaram, P.; Ramakrishnan, V. T.; Venkatachalapathy, B.; Srividya, N.; Ramamurthy, P.; Gunasekaran, K.; Velmurugan, D. J. Chem. Soc. Perkin. Trans. 1998, 2, 999.
Tu, S. J.;Miao, C.; Gao, Y.; Fang, F.; Zhuang, Q.; Feng, Y.; Shi, D. Synlett. 2004, 255.
Das, B.; Thirupathi, P.; Mahender, I.; Reddy, V. S.; Rao, Y. K. J. Mol. Catal. A: Chem. 2006, 247, 233.
Wang, X. Sh.; Zhang, M. M.; Zeng, Z. S.; Shi, D. Q.; Tu, Sh. J.; Wei, X. Y.; Zong, Z. M. Arkivoc. 2006, 2, 117.
Suarez, M.; Loupy, A.; Salfarn, E.; Moran, L.; Rolando, E. Heterocycles. 1999, 51, 21.
Jin, T. S.; Zhang, J. S.; Guo, T. T.; Wang, A. Q.; Li, T. S. Synthesis. 2004, 2001.
Davoodnia, A.; Zare-Bidaki, A.; Behmadi, H. Chin. J. Catal. 2012, 33, 1797.
Dabiri, M.; Baghbanzadeh, M.; Arzroomchilar, E. Catal. Commun. 2008, 9, 939.
Okuhara, T. Chem. Rev. 2002, 102, 3641.
Yassaghi, Gh.; Davoodnia, A.; Allameh, S.; Zare-Bidaki, A.; Tavakoli-Hoseini N. Bull. Korean Chem. Soc. 2012, 33, 2724.
Norouzi, N.; Davoodnia, A.; Bakavoli, M.; Zeinali-Dastmalbaf, M.; Tavakoli-Hoseini, N.; Ebrahimi, M. Bull. Korean Chem. Soc. 2011, 32, 2311.
Kemdeo, S. M.; Sapkal, V.S.; Chaudhari, G.N. J. Mol. Cat. A: Chem. 2011, 323, 70.
Ma’mani, L.; Sheykhan, M.; Heydari, A. Applied Catalysis A: General. 2011, 395, 34.
Shen, K.; Liu, X.; Lu, G.; Miao, Y.; Guo, Y.; Wang, Y. J. Mol. Cat. A: Chem. 2013, 373, 78.
Umbarkar, S. B.; Biradar, A. V.; Mathew, S. M.; Shelke, S. B.; Malshe, K. M.; Patil, P. T.; Dagde, S. P.; Niphadkara, S. P.; Dongare, M. K. Green Chem. 2006, 8, 488.
Khojastehnezhad, A.; Rahimizadeh, M.; Eshghi, H.; Moeinpour, F.; Bakavoli, M. Chin. J. Cat. 2014, 35, 376.
Khojastehnezhad, A.; Rahimizadeh, M.; Moeinpour, F.; Eshghi, H.; Bakavoli, M. Compt. Rend. Chim. 2013, 17, 459.
Khojastehnezhad, A.; Moeinpour, F.; Shams, A. R. Synth. React. Inorg. Met. Org. Chem. 2012, 42, 273.
Khojastehnezhad, A.; Moeinpour, F.; Davoodnia, A. Chin. Chem. Lett. 2011, 22, 807.
Khojastehnezhad, A.; Davoodnia, A.; Bakavoli, M.; Tavakoli-Hoseini, N.; Zeinali-Dastmalbaf, M. Chin. J. .Chem. 2011, 29, 297.
Davoodnia, A.; Khojastehnezhad, A.; Tavakoli-Hoseini, N.; Bakavoli, M. Chin. J. Chem. 2011, 29, 978.
Davoodnia, A.; Khojastehnezhad, A. J. Chil. Chem. Soc. 2012, 57, 1385.
Davoodnia, A.; Khojastehnezhad, A.; Tavakoli-Hoseini, N. Bull. Korean. Chem. Soc. 2011, 32, 2243.
Umbarkara, Sh. B.; Kotbagia, T. P.; Ankush Biradara, V.; Pasrichab, R.; Chanalea, J.; Dongarea, M. K.; Mamedec, A. S.; Lancelot, Ch.; Payenc, E. J. Mol. Catal. A: Chem. 2009, 310, 150.
Deltcheff, C. R.; Aouissi, A.; Bettahar, M. M.; Launey, S.; Fournier, M. J. Catal. 1996, 164, 16.
Kido, A.; Iwamoto, H.; Azuma, N.; Ueno, A. Catal. Surv. Asia. 2002, 6, 45.
Parghi, K. D.; Jayaram, R. V. Catal. Comm. 2010, 11, 1205.
Balalaie, S.; Chadegani, F.; Darviche, F.; Bijanzadeh, H. R. Chin. J. Chem. 2009, 27, 1953.
Mohammadi, G.; Badiei A. R.; Hassanzadeh, M.; Mousavi, S. Arab. J. Chem. 2011, doi:10.1016/j.arabjc.2011.01.037.
Shen, W.; Wang, L.; Tian, T.; Tang, J.; Yu, J. J. Fluorine. Chem. 2009, 130, 522.
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