Microwave Assisted, Silica Gel Mediated, Solvent Free, Michael-Addition of Aryl Methyl Ketones with Chalcones for the Synthesis of 1,3,5-triarylpentane-1,5-diones
DOI:
https://doi.org/10.29356/jmcs.v66i3.1706Keywords:
1,5-diketone, Silica gel, Microwave, Michael addition, 1,5-dicarbonyl compoundsAbstract
Abstract. A series of symmetrical/unsymmetrical 1,3,5-Triarylpentane-1,5-diketone derivatives have been prudently synthesized via direct Michael addition of Chalocones with Aryl Methyl Ketones using microwave irradiation using Silica gel without any solvents. This method affords several advantages such as operational simplicity, short reaction time and easy work up by recrystallization and excellent yields.
Resumen. Se prepararó una serie de derivados simétricos y asimétricos de 1,3,5-triaril-1,5-pentanodiona, a través de la adición de Michael entre arilmetilcetonas y chalconas empelando microondas y gel de sílice con y sin disolvente. El método ofrece ventajas como simplicidad operativa, reducción de los tiempos de reacción y fácil procesamiento por recristaización, así como excelentes rendimientos.
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References
Yoshizawa, K.; Toyota, S.; Toda, F. Tetrahedron Lett. 2001, 42, 7983-7985.
Toda, F.; Suzuki, T.; Higa, S. J. Chem. Soc., Perkin Trans. 1998, 1, 3521-3522.
Trost, B. M.; Semmelhack, M. F.; Flemming, I. Comprehensive Organic Synthesis, 1st ed., 1991, Vol. 4, 1.
Trost, B. M.; Heathcock, C. H.; Fleming, I. Comprehensive Organic Synthesis, 1st ed., 1991, Vol. 2, 133.
Leonard, J. Contemp. Org. Synth. 1994, 387-415.
Leonard, J.; Díez-Barra, S.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061.
Yang, J.; Tao, X.; Yuan, C.; Yan, Y.; Wang, L.; Liu, Z.; Ren, Y.; Jiang, M. J. Am. Chem. Soc. 2005, 127, 3278-3279.
Smith, N. M.; Raston, C. L.; Smith, B. C.; Sobolev, A. N. Green Chem. 2007, 9, 1185-1190.
Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109-2114.
Varala, R.; Alam, M. M.; Adapa, S. R. Synlett. 2003, 720-722.
Alam, M. M.; Varala, R.; Adapa, S. Tetrahedron Lett. 2003, 44, 5115-5119.
Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett., 2005, 46, 1721-1724.
Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 46, 2479-2482.
Chu, C-Fa. Tetrahedron Lett. 2005, 46, 4971-4974.
Liu, B.; Wang, J.; Pang, Y.; Ge, Z.; Li, R. Tetrahedron. 2014, 70, 9240-9244.
Shvekhgeimer, G. A. Chem. Heterocycl. Compd. 1994, 30, 633-660.
Cella, R.; Stefani, A. Tetrahedron. 2013, 65, 2619-2641.
Mason, T. J. Chem. Soc. Rev. 1997, 26, 443-451.
Liju, W.; Ablajan, K.; Juni, F. Ultrason. Sonochem. 2015, 22, 113-118.
Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285-1288.
Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron. 1986, 42, 4777-4786.
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207-222.
Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779-783.
Takahashi, A.; Yanai, H.; Taguchi, K. Chem. Commun. 2008, 2385-2387.
Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152-6153.
Brewster, J. H.; Eliel, E. L. InOrganic Reactions; Adams, R., Eds; John Wiley and Sons: New York, 1953, Vol. 7, 99197.
Constable, E. C.; Harverson, P.; Smith, D. R.; Whall, L. A. Tetrahedron. 1994, 50, 7799-7806.
Onitsuka, S.; Jin, Y. Z.; Shaikh, A. C.; Furuno, H.; Inanaga, J. Molecules. 2012, 17, 11469-11483.
Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845-1848.
Shaabani, A.; Rahmati, A.; Rezayan, A. H.; Darvishi, M.; Badri, Z.; Sarvari, A. QSAR Comb. Sci. 2007, 26, 973-979.
Chauhan, S. S.; Joshi, Y. C. Rasayan, J. Chem. 2008, 3, 475-480.
Jain, A. Kr.; Singla, R. K. Pharmacologyonline. 2011, 3, 244-253.
Guo, F.; Konkol, L. C.; Thomson, R. J. J. Am. Chem. Soc. 2011, 133, 18-20.
Kim, S. H.; Lim, J. W.; Lim, C. H.; Kim, J. N. Bull. Korean Chem. Soc. 2012, 33, 620-624.
Lee, B.; Kang, P.; Lee, K. H.; Cho, J.; Nam, W.; Lee, W. K.; Hur, N. H. Tetrahedron Lett. 2013, 54, 1384-1388.
Smith, N. M.; Corry, B.: Swaminathan Iyer, K.; Norret, M.; Raston, C. L. Lab Chip 2009, 9, 2021-2025.
Ravindran, G.; Renganathan, N. G. Org. Commun. 2010, 3, 76-83.
Hussain, H. T.; Osama, M.; Hussain, W. Int. J. Pharm. Sci. Res. 2014, 5, 2084-2094.
Schmidt, Y.; Bidusenko, I.; Protsku, N.; Ushakov, I.; Trofimov, B. Eur. J. Org. Chem. 2013, 2453-2460.
Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563-2591.
Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.; Trindade, A. F. Chemical Rev. 2009, 109, 2703-2802.
Paul, N.; Shanmugam, M. J.; Muthusubramanian, S. Synth Commun. 2013, 43, 129-138.
Nguyen, K.; Lupton, D. W.; Aust. J. Chem. 2017, 70, 436-441.
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