nano CeO2 as an efficient catalyst for the Synthesis of Azo Dyes
Subject Areas :
1 - استادیار گروه شیمی، دانشگاه پیام نور، تهران، ایران.
Keywords: benzaldehyde derivatives, Azo dye, Naphthol, nano CeO2, xanthen,
Abstract :
Azo compounds are widely used in the pharmaceutical, cosmetic, food, dyeing/textile industries, optics, biochemistry, biophysics and analytical chemistry due to their special physical, chemical and biological properties. In the present study, the synthesis of azo dyes based on naphthols, xanthenes and hydroxy coumarins in the presence of nano- CeO2 catalyst was investigated. Avoid harmful solvents for the environment, mild conditions, high speed and short reaction time, simplicity of working up process; high efficiency and purity of the synthesized derivatives and recoverable catalyst utilization were the advantages of the proposed method. The structure of the synthesized compounds was determined by comparing their physical properties with reported and using IR and HNMR spectroscopy data.The structure of the synthesized compounds was determined by comparing their physical properties with reported and using IR and HNMR spectroscopy data.The structure of the synthesized compounds was determined by comparing their physical properties with reported and using IR and HNMR spectroscopy data.
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[53] Bamoniri A.; Mirjalili B.B.F.; Fouladgari S.; Moshtael-Arani N.; Natl. Acad. Sci. Lett. 39, 25-28, 2016.
_||_[1] Zollinger, H.; “Color Chemistry, Synthesis, Propertiesand Application of Organic Dyes and Pigments”, Wiley-VCH, Weinheim, 2003.
[2] Gregory, P.;”High-Technology Applications of Organic Colorants”, Plenum Press, New York, 1991.
[3] Viscardi, G.; Quagliotto, P.; Barolo, C.; Caputo, G.; Digilio, G.; Degani, I.; Barni, E. Dye.; Pigment. 57, 8-92, 2003.
[4] Clark, J.H.; “Chemistry of Waste Minimization”, Chapman and Hall, London, 1995.
[5] Tanaka, K.; “Solvent-free Organic Synthesis”, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2003.
[6] Morsy, A.; El-Apasery, M.; J. Appl. Polym. Scienc. 109, 695-699, 2008.
[7] Noroozi-Pesyan, N.; Khalafy, J.; Malekpoor, Z. Color. Colorant. Coat. 2, 61-68, 2009.
[8] Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M.; Chem. Rev. 106, 4622–4643, 2006.
[9] Mandic, Z.; Nigovic, B.; Simunic, B.; Electro. Acta. 49, 607–615, 2004.
[10] Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M.; Nature 382, 522–524, 1996.
[11] Steinstrasser, R.; Pohl, L.; Angew. Chem. Int. Ed. 12, 617–630, 1973.
[12] He, Y.; Gu, X.; Guo, M.; Wang, X.; Optic. Material. 31, 18–27, 2008.
[13] Pieraccini, S.; Masiero, S.; Spada, G.; Gottarelli, G.; Chem. Commun. 9, 598–599, 2003.
[14] Merino, E.; Chem. Soc. Rev. 40, 3835–3853, 2011.
[15] Mirjalili, B.F.; Bamoniri, A.; Akbari, A.; Curr. Chem. Lett. 1,109–114, 2012.
[16] Bokare, A.D.; Chikate, R.C.; Rode, C.V.; Paknikar, K.M.; Appl. Catal. B. 79, 270–278, 2008.
[17] Qian, H.; Jiang, D.E.; Li, G.; Gayathri, C.; Das, A.; Gil, R.R.; Jin, R.; J. Am. Chem. Soc. 134,16159–62, 2012.
[18] Hosseini-Sarvari, M. J. Rapid. Commun. Synth. Org. Chem. 38, 832-841, 2008.
[19] Hay, A.E.; Aumond, M.C.; Mallet, S.; Dumontet, V.; Litaudon, M.; Rondeau, D.; Richomme, P.; J. Natur. Prod. 67, 707–709, 2004.
[20] Zelefack, F.; Guilet, D.; Fabre, N.; Bayet, C.; Chevalley, S.V.; Ngouela, S.R.; Lenta, B.N.; Valentin, S.; Tsamo, E.; Dijoux-Franca, M.V.; J. Natur. Prod. 72, 954–957, 2009.
[21] Khurana, J.M.; Magoo, D.; Aggarwal, K.; Aggarwal, N.; Kumar, R.; Srivastava, C.; Europ. J. Med. Chem. 58, 470–477, 2012.
[22] Niu, S.L.; Li, Z.L.; Ji, F.; Liu, G.Y.; Zhao, N.; Liu, X.O.; Jing, Y.K.; Hua, H.M.; Phytochem. 77, 280–286, 2012.
[23] Laphookhieo, S.; Syers, J.K.; Kiattansakul, R.; Chantrapromma, K.; Chem. Pharm. Bull. 54, 745–747, 2006.
[24] Llama, E.F.; del Campo, C.; Capo, M.; Anadon, M.; Europ. J. Med. Chem. 24(4), 391–396, 1989.
[25] Omolo, J.J.; Johnson, M.M.; Van Vuuren, N.S.F.; De Koning, C.B.; Bioorg. Med. Chem. Lett. 21, 7085–7088, 2011. [26] Jamison, J.M.; Krabill,K.; Hatwalkar, A.; Jamison, E.; Tsai, C.C.; Cell Biology. Int. Report. 14, 1075–1084, 1990.
[27] Hafez, H.N.; Hegab, M.I.; Ahmed-Farag, I.S.; El-Gazzar, A.B.A.; Bioorg. Med. Chem. Lett. 18, 4538–4543, 2008.
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[29] Chen, X.;. Pradhan, T.; Wang, F.; Kim, J.S.; Yoon, S.; Chem. Rev. 112, 1910- 1956, 2011.
[30] Li, M.; Li, J.; Liu, B.; Zhou, Y.; Li, X.; Xue, X.; Hou, Z.; Luo, X.; Europ. J. Pharmacol. 721, 151-155, 2013.
[31] O’Reilly, R.; Ohms, J.; Motley, C.; J. Biology. Chem. 244, 1303-1338, 1969.
[32] Zhao, H.; Neamati, N.; Hong, H.;. Mazumder, A.; Wang, S.; Sunder, S.; Milne, G.W.A.; Pommier, T.R.; Burke, Jr.; J. Med. Chem. 40, 242-246, 1997.
[33] Manolov, I.; Dimitrov, I.; Danchev, N.; Kostadinova, I.; World. J. Research. Rev. 3, 50-62, 2016.
[34] Sen, K.; Bagchi, P.; J. Org. Chem. 24, 316-320, 1959.
[35] Węglarz-Tomczak, E.; Górecki, L.; Chemik. 66, 1298–307, 2012.
[36] Zhen, W.; Han, H.; Anguiano, M.; Lemere, C.; Cho, C.G.; Lansbury, P.T.; J. Med. Chem. 42, 2805–2815, 1999.
[38] Kwasi Adu, J.; Amengor, C.D.K.; Mohammed, N.;J. Tropical. Medicine. 2, 1-8, 2020.
[39] Davasaz Rabbani, M.A.; Khalili, B.; Saeidian, H.; RSC Adv. 10, 35729-35739, 2020.
[40] Badrey, M.G.; Gomha, S.M.; Mashaly, H.M.; Eur. J. Chem. 7, 146-151, 2016.
[41] Gur, M. J. Het. Chem. 56, 980-987, 2019.
[42] Noroozi Pesyana, N.; Gholsanamlooa,V.; Moradi Parb, M.; Iran. Chem. Commun. 7, 1-9, 2019.
[43] Muthuchudarkodi, R.R.; Kalaiarasi, S.; J. Sci. Research. 5, 543-547, 2013.
[44] Bamoniri, A.; Moshtael-Arani, N.; RSC Advanc. 5, 16911–16920, 2015.
[45] Bamonori, A.; Mirjalili, B.B.; National. Academ. Sci. Lett. 39, 25-28, 2016.
[46] Rahimizadeh, M.; Eshghi, H.; Shiri, A.; Ghadamyari, Z.; Matin, M.M.; Oroojalian, F.; Pordeli, P.; J.; Korean. Chem. Soc. 56, 716-719, 2012.
[47] Ghaffari, N.; Abd Hamid, Sh.; Hazarkhanic, H.; Inorg. Nano. Metal. Chem. 47, 1-26, 2017.
[48] Zarei, A.; Hajipour, A.R.; Khazdooz, L.; Mirjalili, B.F.; Najafi, Dye. Pigment. 81, 240-244, 2009.
[49] Bamoniri, A.; Mirjalili, B. B. F.; Ghorbani-Choghamarani, A.; Yazdanshenas, M. E.; Shayanfar, A.; Akbari, A.
Iran. J. Org. Chem. 3, 603-606, 2011.
[50] Ginni, S.; Karnawat, R.; Sharma, I. K.; Verma P.S. Int. J. A. Bio. Pharm. Technol. 2, 332-338, 2011.
[51] Bamoniri, A.; Pourali, A.R.; Nazifi, S. M.R. Iran. J. Catal. 4, 185-189, 2012.
[52] Bamoniri, A.; Mirjalili, B.B.F.; Ghorbani-Choghamarani A.; Yazdanshenas M.E.; Shayanfar A.; Akbari A. Iran. J. Catal. 1, 51-54, 2011.
[53] Bamoniri A.; Mirjalili B.B.F.; Fouladgari S.; Moshtael-Arani N.; Natl. Acad. Sci. Lett. 39, 25-28, 2016.
