Catalyst-free, a Green, and Efficient Protocol for the Synthesis of 1,8-dioxooctahydroxanthenes in Magnetized Water
DOI:
https://doi.org/10.29356/jmcs.v63i4.865Keywords:
1,8-dioxooctahydroxanthenes, catalyst-free, magnetized waterAbstract
In this paper, we report the catalyst-free three-component synthesis of 1,8-dioxooctahydroxanthenes in magnetized water as a green solvent. The reaction of aldehydes and 1,3-cyclohexanedione/dimedone in magnetized water gives the 9-substituted 1,8-dioxooctahydroxanthene derivatives. This green method offers the advantages of short reaction times, low-cost, simple work-up procedure, quantitative reaction yields, and no need for an organic solvent.
Downloads
References
Wan, Y.; Zhang, X. X.; Wang, C.; Zhao, L. L.; Chen, L. F.; Liu, G. X.; Huang, S. Y.; Yue, S. N.; Zhang, W. L.; Wu, H. Tetrahedron 2013, 13, 3947-3950. DOI: https://doi.org/10.1016/j.tet.2013.03.029
Jamison, J. M.; Krabill, K.; Hatwalkar, A.; Jamison, E.; Tsai, C. C. Cell biology international reports 1990, 1, 1075-1084. DOI: https://doi.org/10.1016/0309-1651(90)90015-Q
Rewcastle, G. W.; Atwell, G. J.; Zhuang L.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1991, 11, 217-222. DOI: https://doi.org/10.1021/jm00105a034
Mulakayala, N.; Murthy, P. V.; Rambabu, D.; Aeluri, M.; Adepu, R.; Krishna, G. R.; Reddy, C. M.; Prasad, K. R.; Chaitanya, M.; Kumar, C. S.; Rao, M. B. Bioorg. Med. Chem. Lett. 2012, 6, 2186-2191. DOI: https://doi.org/10.1016/j.bmcl.2012.01.126
Srihari, P.; Mandal, S. S.; Reddy, J. S.; Rao, R. S.; Yadav, J. S. Chin. Chem. Lett. 2008, 7, 771-774. DOI: https://doi.org/10.1016/j.cclet.2008.05.005
Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 6, 8551-8588. DOI: https://doi.org/10.1016/j.tet.2005.05.043
Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H.; Lee, J. J. Phys. D: Appl. Phys. 2002, 5, 1473-1476. DOI: https://doi.org/10.1088/0022-3727/35/13/303
Das, B.; Thirupathi, P.; Reddy, K. R.; Ravikanth, B.; Nagarapu, L. Catal. Commun. 2007, 8, 535-538. DOI: https://doi.org/10.1016/j.catcom.2006.02.023
Maghsoodlou, M. T.; Habibi-Khorassani, S. M.; Shahkarami, Z.; Maleki, N.; Rostamizadeh, M. Chin. Chem. Lett. 2010, 6, 686-689. DOI: https://doi.org/10.1016/j.cclet.2010.02.005
Xia, J. J.; Zhang, K. H. Molecules 2012, 5, 5339-5345. DOI: https://doi.org/10.3390/molecules17055339
11 Mokhtary, M.; Langroudi, S. A. Monatsh. Chem. 2014, 9, 1489-1494.
Hazeri, N.; Masoumnia, A.; Mghsoodlou, M. T.; Salahi, S.; Kangani, M.; Kianpour, S.; Kiaee, S.; Abonajmi, J. Res. Chem. Intermed. 2015, 7, 4123-4131. DOI: https://doi.org/10.1007/s11164-013-1516-2
Dadhania, A. N.; Patel, V. K.; Raval, D. K. Compt. Rend. Chim. 2012, 5, 378-383. DOI: https://doi.org/10.1016/j.crci.2012.01.006
Venkatesan, K.; Pujari, S. S.; Srinivasan, K. V. Synth. Commun. 2008, 2, 228-241. DOI: https://doi.org/10.1080/00397910802044306
Ball. P. A Bibliography of Water. Phoenix Press, 2000, 9, 373-387. DOI: https://doi.org/10.1002/9781118032886.biblio
Pang, X. F. Chin. J. Atom. Mol. Phys. 2006, 7, 1-3.
Pang, X. F. Eur. Phys. J. B. 2006, 1, 5-23. DOI: https://doi.org/10.1140/epjb/e2006-00020-6
18 Grewal, H. S.; Maheshwari, B. L. Bioelectromagnetics 2011, 1, 58-65. DOI: https://doi.org/10.1002/bem.20615
Pang, X. F.; Deng, B.; Tang, B. Mod. Phys. Lett. B. 2012, 11, 1250-1269.
Chang, K. T.; Weng, C. I. J. Appl. Phys. 2006, 4, 043917.
Guo, Y. Z.; Yin, D. C.; Cao, H. L.; Shi, J. Y.; Zhang, C. Y.; Liu, Y. M.; Huang, H. H.; Liu, Y.; Wang, Y.; Guo, W. H.; Qian, A. RInt. J. Mol. Sci. 2012, 12, 16916-16928. DOI: https://doi.org/10.3390/ijms131216916
Baran, B.; Berezyuk, O.; Golonzhka, V. Environ. Eng. Manag. J. 2006, 38, 19-23.
Gang, N.; St-Pierre, L.; Persinger, M. Water 2012, 3, 122-131.
Higashitani, K.; Oshitani, J.; Ohmura, N. Colloids Surf. A 1996, 109, 167-173. DOI: https://doi.org/10.1016/0927-7757(95)03483-8
Bakherad, M.; Keivanloo, A.; Gholizadeh, M.; Doosti, R.; Javanmardi, M. Res. Chem. Intermed. 2017, 43, 1013-1029. DOI: https://doi.org/10.1007/s11164-016-2680-y
Bakherad, M.; Moosavi, F.; Keivanloo, A.; Doosti, R.; Moradian, E.; Armaghan, M. Res. Chem. Intermed. 2019, 45, 2981-2997. DOI: https://doi.org/10.1007/s11164-019-03774-8
Bakherad, M.; Doosti, R.; Keivanloo, A.; Gholizadeh, M.; Jadidi, K. J. Iran. Chem. Soc. 2017, 14, 2591-2597. DOI: https://doi.org/10.1007/s13738-017-1193-y
Bakherad, M.; Doosti, R.; Keivanloo, A.; Gholizadeh, M.; Amin, A. H. Lett. Org. Chem. 2017, 14, 510-516. DOI: https://doi.org/10.2174/1570178614666170511170329
Bakherad, M.; Moosavi, F.; Doosti, R.; Keivanloo, A.; Gholizadeh, M. New J. Chem. 2018, 42, 4559-4566. DOI: https://doi.org/10.1039/C7NJ03471G
John, A.; Yadav, P. J.; Palaniappan, S. J. Mol. Catal. A: Chem. 2006, 2, 121-125. DOI: https://doi.org/10.1016/j.molcata.2005.12.017
Pramanik, A.; Bhat, S. Catal. Commun. 2012, 5, 17-24. DOI: https://doi.org/10.1016/j.catcom.2011.12.036
Song, G.; Wang, B.; Luo, H.; Yang, L. Catal. Commun. 2007, 4, 673-676. DOI: https://doi.org/10.1016/j.catcom.2005.12.018
Dabiri, M.; Baghbanzadeh, M.; Arzroomchilar, E. Catal. Commun. 2008, 5, 939-942. DOI: https://doi.org/10.1016/j.catcom.2007.09.023
Mahdavinia, G. H. J. Iran. Chem. Res. 2008, 1, 11-17.
Toledo, E. J.; Ramalho, T. C.; Magriotis, Z. M. J. Mol. Struct. 2008, 888, 409-415. DOI: https://doi.org/10.1016/j.molstruc.2008.01.010
Amoozadeh, A.; Rahmani, S. J. Mol. Catal. A: Chem. 2015, 3, 96-107. DOI: https://doi.org/10.1016/j.molcata.2014.09.020
Shirini, F.; Abedini, M.; Pourhasan, R. Dye. Pig. 2013, 4, 38581–38588.
Gong, K.; Wang, H.; Wang, S.; Wang, Y.; Chen, J. J. Catal. 2015, 8, 1249-1255. DOI: https://doi.org/10.1016/S1872-2067(15)60888-9
Karami, B.; Zare, Z.; Eskandari, K. Chem. Pap. 2013, 2, 145-154.
Karami, B.; Eskandari, K.; Zare, Z.; Gholipour, S. Chem. Heterocycl. Comp. 2014, 12, 1715-1722. DOI: https://doi.org/10.1007/s10593-014-1423-5
Shaterian, H. R.; Rigi, F. Res. Chem. Intermed. 2015, 2, 721-738. DOI: https://doi.org/10.1007/s11164-013-1223-z
Shirini, F.; Yahyazadeh, A.; Mohammadi, K. Chin. Chem. Lett. 2014, 2, 341-347. DOI: https://doi.org/10.1016/j.cclet.2013.11.016
Mokhtary, M.; Langroudi, S. A. Monatsh. Chem. 2014, 9, 1489-1494. DOI: https://doi.org/10.1007/s00706-014-1206-9
Rafiee, E.; Eavani, S.; Khodayari, M. Chin. J. Catal. 2013, 8, 1513-1518. DOI: https://doi.org/10.1016/S1872-2067(12)60645-7
Ilangovan, A.; Muralidharan, S.; Sakthivel, P.; Malayappasamy, S.; Karuppusamy, S.; Kaushik, M. P. Tetrahedron Lett. 2013, 6, 491-494. DOI: https://doi.org/10.1016/j.tetlet.2012.11.058


Downloads
Additional Files
Published
Issue
Section
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.
