Catalyst-free, a Green, and Efficient Protocol for the Synthesis of 1,8-dioxooctahydroxanthenes in Magnetized Water

  • Mohammad Bakherad Shahrood University of Technology
  • Ali Keivanloo Shahrood University of Technology
  • Amir Amin Shahrood University of Technology
  • Amir Farkhondeh Shahrood University of Technology
Keywords: 1,8-dioxooctahydroxanthenes, catalyst-free, magnetized water

Abstract

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.

Author Biographies

Mohammad Bakherad, Shahrood University of Technology

Faculty of Chemistry

Ali Keivanloo, Shahrood University of Technology

Faculty of Chemistry

Amir Amin, Shahrood University of Technology

Faculty of Chemistry

Amir Farkhondeh, Shahrood University of Technology

Faculty of Chemistry

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.

Jamison, J. M.; Krabill, K.; Hatwalkar, A.; Jamison, E.; Tsai, C. C. Cell biology international reports 1990, 1, 1075-1084.

Rewcastle, G. W.; Atwell, G. J.; Zhuang L.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1991, 11, 217-222.

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.

Srihari, P.; Mandal, S. S.; Reddy, J. S.; Rao, R. S.; Yadav, J. S. Chin. Chem. Lett. 2008, 7, 771-774.

Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 6, 8551-8588.

Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H.; Lee, J. J. Phys. D: Appl. Phys. 2002, 5, 1473-1476.

Das, B.; Thirupathi, P.; Reddy, K. R.; Ravikanth, B.; Nagarapu, L. Catal. Commun. 2007, 8, 535-538.

Maghsoodlou, M. T.; Habibi-Khorassani, S. M.; Shahkarami, Z.; Maleki, N.; Rostamizadeh, M. Chin. Chem. Lett. 2010, 6, 686-689.

Xia, J. J.; Zhang, K. H. Molecules 2012, 5, 5339-5345.

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.

Dadhania, A. N.; Patel, V. K.; Raval, D. K. Compt. Rend. Chim. 2012, 5, 378-383.

Venkatesan, K.; Pujari, S. S.; Srinivasan, K. V. Synth. Commun. 2008, 2, 228-241.

Ball. P. A Bibliography of Water. Phoenix Press, 2000, 9, 373-387.

Pang, X. F. Chin. J. Atom. Mol. Phys. 2006, 7, 1-3.

Pang, X. F. Eur. Phys. J. B. 2006, 1, 5-23.

18 Grewal, H. S.; Maheshwari, B. L. Bioelectromagnetics 2011, 1, 58-65.

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.

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.

Bakherad, M.; Keivanloo, A.; Gholizadeh, M.; Doosti, R.; Javanmardi, M. Res. Chem. Intermed. 2017, 43, 1013-1029.

Bakherad, M.; Moosavi, F.; Keivanloo, A.; Doosti, R.; Moradian, E.; Armaghan, M. Res. Chem. Intermed. 2019, 45, 2981-2997.

Bakherad, M.; Doosti, R.; Keivanloo, A.; Gholizadeh, M.; Jadidi, K. J. Iran. Chem. Soc. 2017, 14, 2591-2597.

Bakherad, M.; Doosti, R.; Keivanloo, A.; Gholizadeh, M.; Amin, A. H. Lett. Org. Chem. 2017, 14, 510-516.

Bakherad, M.; Moosavi, F.; Doosti, R.; Keivanloo, A.; Gholizadeh, M. New J. Chem. 2018, 42, 4559-4566.

John, A.; Yadav, P. J.; Palaniappan, S. J. Mol. Catal. A: Chem. 2006, 2, 121-125.

Pramanik, A.; Bhat, S. Catal. Commun. 2012, 5, 17-24.

Song, G.; Wang, B.; Luo, H.; Yang, L. Catal. Commun. 2007, 4, 673-676.

Dabiri, M.; Baghbanzadeh, M.; Arzroomchilar, E. Catal. Commun. 2008, 5, 939-942.

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.

Amoozadeh, A.; Rahmani, S. J. Mol. Catal. A: Chem. 2015, 3, 96-107.

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.

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.

Shaterian, H. R.; Rigi, F. Res. Chem. Intermed. 2015, 2, 721-738.

Shirini, F.; Yahyazadeh, A.; Mohammadi, K. Chin. Chem. Lett. 2014, 2, 341-347.

Mokhtary, M.; Langroudi, S. A. Monatsh. Chem. 2014, 9, 1489-1494.

Rafiee, E.; Eavani, S.; Khodayari, M. Chin. J. Catal. 2013, 8, 1513-1518.

Ilangovan, A.; Muralidharan, S.; Sakthivel, P.; Malayappasamy, S.; Karuppusamy, S.; Kaushik, M. P. Tetrahedron Lett. 2013, 6, 491-494.

Published
12-09-2019