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.
Downloads
References
Yoshizawa, K.; Toyota, S.; Toda, F. Tetrahedron Lett. 2001, 42, 7983-7985. DOI: https://doi.org/10.1016/S0040-4039(01)01562-3
Toda, F.; Suzuki, T.; Higa, S. J. Chem. Soc., Perkin Trans. 1998, 1, 3521-3522. DOI: https://doi.org/10.1039/a805884i
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. DOI: https://doi.org/10.1016/B978-0-08-052349-1.00027-5
Leonard, J. Contemp. Org. Synth. 1994, 387-415. DOI: https://doi.org/10.1039/co9940100387
Leonard, J.; Díez-Barra, S.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061. DOI: https://doi.org/10.1002/(SICI)1099-0690(199810)1998:10<2051::AID-EJOC2051>3.3.CO;2-K
Yang, J.; Tao, X.; Yuan, C.; Yan, Y.; Wang, L.; Liu, Z.; Ren, Y.; Jiang, M. J. Am. Chem. Soc. 2005, 127, 3278-3279. DOI: https://doi.org/10.1021/ja043510s
Smith, N. M.; Raston, C. L.; Smith, B. C.; Sobolev, A. N. Green Chem. 2007, 9, 1185-1190. DOI: https://doi.org/10.1039/b700893g
Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109-2114. DOI: https://doi.org/10.1021/jo026550s
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. DOI: https://doi.org/10.1016/S0040-4039(03)01089-X
Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett., 2005, 46, 1721-1724. DOI: https://doi.org/10.1016/j.tetlet.2005.01.051
Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 46, 2479-2482. DOI: https://doi.org/10.1016/j.tetlet.2005.02.044
Chu, C-Fa. Tetrahedron Lett. 2005, 46, 4971-4974. DOI: https://doi.org/10.1016/j.tetlet.2005.05.099
Liu, B.; Wang, J.; Pang, Y.; Ge, Z.; Li, R. Tetrahedron. 2014, 70, 9240-9244. DOI: https://doi.org/10.1016/j.tet.2014.10.009
Shvekhgeimer, G. A. Chem. Heterocycl. Compd. 1994, 30, 633-660. DOI: https://doi.org/10.1007/BF01166304
Cella, R.; Stefani, A. Tetrahedron. 2013, 65, 2619-2641. DOI: https://doi.org/10.1016/j.tet.2008.12.027
Mason, T. J. Chem. Soc. Rev. 1997, 26, 443-451. DOI: https://doi.org/10.1039/cs9972600443
Liju, W.; Ablajan, K.; Juni, F. Ultrason. Sonochem. 2015, 22, 113-118. DOI: https://doi.org/10.1016/j.ultsonch.2014.05.013
Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285-1288. DOI: https://doi.org/10.1039/jr9350001285
Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron. 1986, 42, 4777-4786. DOI: https://doi.org/10.1016/S0040-4020(01)82058-5
Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207-222. DOI: https://doi.org/10.1021/ja00885a021
Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779-783. DOI: https://doi.org/10.1246/bcsj.49.779
Takahashi, A.; Yanai, H.; Taguchi, K. Chem. Commun. 2008, 2385-2387. DOI: https://doi.org/10.1039/b800815a
Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152-6153. DOI: https://doi.org/10.1021/ja00799a072
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. DOI: https://doi.org/10.1016/S0040-4020(01)85263-7
Onitsuka, S.; Jin, Y. Z.; Shaikh, A. C.; Furuno, H.; Inanaga, J. Molecules. 2012, 17, 11469-11483. DOI: https://doi.org/10.3390/molecules171011469
Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845-1848. DOI: https://doi.org/10.1016/0040-4039(96)00159-1
Shaabani, A.; Rahmati, A.; Rezayan, A. H.; Darvishi, M.; Badri, Z.; Sarvari, A. QSAR Comb. Sci. 2007, 26, 973-979. DOI: https://doi.org/10.1002/qsar.200620024
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. DOI: https://doi.org/10.1021/ja108717r
Kim, S. H.; Lim, J. W.; Lim, C. H.; Kim, J. N. Bull. Korean Chem. Soc. 2012, 33, 620-624. DOI: https://doi.org/10.5012/bkcs.2012.33.2.620
Lee, B.; Kang, P.; Lee, K. H.; Cho, J.; Nam, W.; Lee, W. K.; Hur, N. H. Tetrahedron Lett. 2013, 54, 1384-1388. DOI: https://doi.org/10.1016/j.tetlet.2012.12.106
Smith, N. M.; Corry, B.: Swaminathan Iyer, K.; Norret, M.; Raston, C. L. Lab Chip 2009, 9, 2021-2025. DOI: https://doi.org/10.1039/b902986a
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. DOI: https://doi.org/10.1002/ejoc.201201700
Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563-2591. DOI: https://doi.org/10.1021/cr0509410
Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.; Trindade, A. F. Chemical Rev. 2009, 109, 2703-2802. DOI: https://doi.org/10.1021/cr800462w
Paul, N.; Shanmugam, M. J.; Muthusubramanian, S. Synth Commun. 2013, 43, 129-138. DOI: https://doi.org/10.1080/00397911.2011.593106
Nguyen, K.; Lupton, D. W.; Aust. J. Chem. 2017, 70, 436-441. DOI: https://doi.org/10.1071/CH16566


Downloads
Additional Files
Published
Issue
Section
License
Copyright (c) 2022 Chithiravel Rengasamy, Rajaguru Kandasamy, Muthusubramanian Shanmugam

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
