Environmentally benign synthesis of 14-Phenyl-8H-Dibenzo[a,i]xanthene-8,13(14H)-Diones using CuI nanoparticles as an efficient catalyst

Iranian Journal of Catalysis

مقاله 6، دوره 7، شماره 1، خرداد 2017، صفحه 47-52   

نوع مقاله: Articles

نویسندگان

Javad Safaei-Ghomi^* ؛ Jalal Shapoori؛ Mohammad Ali Ghasemzadeh

Department of Chemistry, Qom Branch, Islamic Azad University, Qom, I. R. Iran.

چکیده

In this study, CuI nanoparticles as an efficient catalyst was used for the synthesis of 14-phenyl-8H-dibenzo[a,i]xanthene-8,13(14H)-diones using aldehydes, 2-naphthol and 2-hydroxynaphthalene-1,4-dione in aqueous media. In this study, it was found that water was the most effective solvent compared to others. Among several catalysts that were tested for this multi-component synthesis, CuI nanoparticles were the best catalyst with 4 mol% loading. The reusability of CuI nanoparticles was experienced for 6 times with a slightly decreased activity. The use of no hazardous organic solvent, atom economy, short reaction times, little catalyst loading, reusability of the catalyst and high yields of products are some of the important features of this protocol.  

کلیدواژه‌ها

Dibenzoxanthene؛ CuI nanoparticles؛ Environmentally benign؛ Three-component reactions

مراجع

[1] H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag, A.B.A. El-Gazzar, Bioorg. Med. Chem. Lett. 18 (2008) 4538-4543.
[2] A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem. 12 (2010) 20-24.
[3] A. Banerjee, A.K. Mukherjee, Stain Technol. 56 (1981) 83-85.
[4] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
[5] C.G. Knight, T. Stephens, Biochem. J. 258 (1989) 683-687.
[6] R.J. Sarma, J.B. Baruah, Dyes Pigm. 64 (2005) 91-92.
[7] S. Ko, C.F. Yao, Tetrahedron Lett. 47 (2009) 8827-8829.
[8] L. Wu, J. Zhang, L. Fang, C. Yang, F. Yan, Dyes Pigm. 86 (2010) 93-96.
[9] M. Dabiri, Z. Noroozi Tisseh, A. Bazgir, J. Heterocycl. Chem. 47 (2010) 1062-1065.
[10] B. Maleki, E. Akbarzadeh, S. Babaee, Dyes Pigm. 123 (2015) 222-234.
[11] A. Rahmati, Chin. Chem. Lett. 21 (2010) 761-764.
[12] A. Bhunia, T. Kaicharla, D. Porwal, R.G. Gonnade, A.T. Biju, Chem. Commun. 50 (2014) 11389-11392.
[13] J. Safaei-Ghomi, M. Asgari-Keirabadi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, Res. Chem. Intermed. 42 (2016) 827-837.
[14] J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, H. Shahbazi-Alavi, RSC Adv. 4 (2014) 46106-46113.
[15] B.M. Goodajdar, S. Soleimani, Iran. J. Catal. 6 (2016) 43-49.
[16] L. Khazdooz, A. Zarei, Iran. J. Catal. 6 (2016) 69-74.
[17] V. Polshettiwar, R.S. Varma, Green Chem. 12 (2010) 743-754.
[18] B.H. Lipshutz, S. Ghorai, W.W.Y. Leong, B.R. Taft, J. Org. Chem. 76 (2011) 5061-5073.
[19] J. Safaei-Ghomi, H. Shahbazi-Alavi, M.R. Saberi-Moghadam, A. Ziarati, Iran. J. Catal. 4 (2014) 289-294.
[20] J. Safaei-Ghomi, M.R. Saberi-Moghadam, H. Shahbazi Alavi, M.Asgari Kheirabadi, J. Chem. Res. 38 (2014) 583-585.
[21] K. Chanda, S. Rej, M.H. Huang, Chem. Eur. J. 19 (2013) 16036-16043.
[22] D. Damodara, R. Arundhathi, P. R. Likhar, Adv. Synth. Catal. 356 (2014) 189-198.
[23] M. Golshekan, S. Shariati, N. Saadatjoo, RSC Adv. 4 (2014) 16589-16596.
[24] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Ultrason. Sonochem. 20 (2013) 1069-1075.
[25] J. Safaei-Ghomi, H. Shahbazi-Alavi, A. Ziarati, R. Teymuri, Chin. Chem. Lett. 25 (2014) 401-405.
[26] A. Ziarati, J. Safaei-Ghomi, S. Rohani, Chin. Chem. Lett. 24 (2013) 195-198.
[27] J. Safaei-Ghomi, A. Ziarati, R. Teymuri, Bull. Korean Chem. Soc. 33 (2012) 2679-2682.
[28] B. Sreedhar, R. Arundhathi, P.L. Reddy, M.L. Kantam, J. Org. Chem. 74 (2009) 7951-7954.
[29] H.J. Xu, Y.F. Liang, Z.Y. Cai, H.X. Qi, C.Y. Yang, Y.S. Feng, J. Org. Chem. 76 (2011) 2296-2300.
[30] N.G. Khaligh, Catal. Sci. Technol. 2 (2012) 2211-2215.
[31] J.M. Khurana, A. Chaudhary, A. Lumb, B. Nand, Can. J. Chem. 90 (2012) 739–746.