Synthesis of dihydrofurans using biosynthesized CuO nanoparticles
الموضوعات : Iranian Journal of CatalysisJavad Safaei-Ghomi 1 , Hossein Shahbazi-Alavi 2
1 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 51167, I. R. Iran.
2 - Young Researchers and Elite Club, Kashan Branch, Islamic Azad University, Kashan, Iran.
الکلمات المفتاحية: Green synthesis, One-pot, Reusable catalyst, Dihydrofurans, Biosynthesized CuO nanoparticles,
ملخص المقالة :
The preparation of trans-dihydrofurans has been achieved by a one-pot condensation reaction of 4-bromophenacyl bromide, aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione using biosynthesized CuO nanoparticles under reflux conditions in ethanol. CuO nanoparticles (CuO NPs) were prepared using extractof leaves of Ajuga chamaecistus Subsp. Scoparia. The key advantages of this process are the diastereoselective synthesis, reusability of the catalyst, low catalyst loading, excellent yields, short reaction times, simple workup and environmentally benign. Fully optimized structures of trans and cis dihydrofurans were obtained by B3LYP/6-31G(d,p) method. The structures of the prepared trans-2,3-dihydrofurans were fully characterized by 1H and 13C NMR spectra, IR spectra, and elemental analysis.
[1] C.P.V. Freire, S.B. Ferreira, N.S.M. de Oliveira, A.B.J. Matsuura, I.L. Gama, F.C. da Silva, M.C.B.V. de Souza, E.S. Lima, V.F. Ferreira, Med. Chem. Commun. 1 (2010) 229–232.
[2] Y. Matsuya, N. Suzuki, S. Kobayashi, T. Miyahara, H. Ochiai, H. Nemoto, Bioorg. Med. Chem. 18 (2010) 1477–1481.
[3] A. Scala, M. Cordaro, F. Risitano, I. Colao, A. Venuti, M.T. Sciortino, P. Primerano, G. Grassi, Mol. Divers. 16 (2012) 325-333.
[4] K. Salat, A. Moniczewski, R. Salat, M. Janaszek, B. Filipek, B. Malawska, K. Wieckowski, Pharmacol. Biochem. Behav. 101 (2012) 138-147.
[5] Y. Zhang, H. Zhong, T. Wang, D. Geng, M. Zhang, K. Li, Eur. J. Med. Chem. 48 (2012) 69-80.
[6] K. Wieckowski, K. Sałat, J. Bytnar, M. Bajda, B. Filipek, J.P. Stables, B. Malawska, Bioorg. Med. Chem. 20 (2012) 6533–6544.
[7] K. Sugimoto, K. Tamura, N. Ohta, C. Tohda, N. Toyooka, H. Nemoto, Y. Matsuya, Bioorg. Med. Chem. Lett. 22 (2012) 449–452.
[8] B.B.F. Mirjalili, L. Zamani, K. Zomorodian, S. Khabnadideh, Z. Haghighijoo, Z. Malakotikhah, S.A. Ayatollahi Mousavi, S. Khojasteh, J. Mol. Struct. 1116 (2016) 102-108.
[9] J. Safaei-Ghomi, S.H. Nazemzadeh, H. Shahbazi-Alavi, Appl. Organometal. Chem. 30 (2016) 911-916.
[10] L. Suresh, P.S.V. Kumar, G.V.P. Chandramouli, J. Mol. Struct. 1134 (2017) 51-58.
[11] W. Cao, W. Ding, J. Chen, Y. Chen, Q. Zang, G. Chen, Synth. Commun. 34 (2004) 1599-1608.
[12] C. Xing, S. Zhu, J. Org. Chem. 69 (2004) 6486-6488.
[13] M. Yilmaz, N. Uzunalioglu, M. Yakut, T. Pekel, Turk. J. Chem. 32 (2008) 411-422.
[14] M. Yilmaz, E. Bicer, A. T. Pekel, Turk. J. Chem. 29 (2005) 579-587.
[15] S. Maiti, P.T. Perumal, J.C. Menendez, Tetrahedron 66 (2010) 9512-9518.
[16] S. Son, G.C. Fu, J. Am. Chem. Soc. 129 (2007) 1046-1047.
[17] S.M. Rajesh, S. Perumal, J.C. Menendez, S. Pandian, R. Murugesan, Tetrahedron 68 (2012) 5631-5636.
[18] A. Kumar, S. Srivastava, G. Gupta, Green Chem. 14 (2012) 3269-3272.
[19] A.T. Khan, M. Lal, R.S. Basha, Synthesis 45 (2013) 406-412.
[20] Q.F. Wang, H. Hou, L. Hui, C.G. Yan, J. Org. Chem. 74 (2009) 7403-7406.
[21] A.K. Mittal, Y. Chisti, U.C. Banerjee, Biotechnol. Adv. 31 (2013) 346–356.
[22] A. Ehsani, R. Asgari, A. Rostami-Vartooni, H. Mohammad Shiri, A. Yeganeh-Faal, Iran. J. Catal. 6 (2016) 269-274.
[23] J. Safaei-Ghomi, M. Asgari-Kheirabadi, H. Shahbazi-Alavi, A. Ziarati, Iran. J. Catal. 6 (2016) 319-324.
[24] F. Camps, J. Coll, Phytochem. 32 (1993) 1361-1370.
[25] H. Chen, R. X. Tan, Z.L. Liu, Y. Zhang, J. Nat. Prod. 59 (1996) 668-670.
[26] T.A. Kutepova, V.N. Syrov, Z.A. Khushbaktova, Z. Saatov, Pharm. Chem. J. 35 (2001) 608-609.
[27] P. Akbay, J. Gertsch, I. Calis, J. Heilmann, O. Zerbe, O. Sticher, Helv. Chem. Acta 85 (2002) 1930-1942.
[28] S. Bouderbala, J. Prost, M.A. Lacaille-Dubois, M. Bouchenak, Nutr. Res. 30 (2010) 358–365.
[29] L. Rout, T.K. Sen, T. Punniyamurthy, Angew. Chem. Int. Ed. 46 (2007) 5583–5586.
[30] D. Alves, C.G. Santos, M.W. Paixao, L.C. Soares, D. de Souza, O.E.D. Rodrigues, A.L. Braga, Tetrahedron Lett. 50 (2009) 6635–6638.
[31] S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, R. Mitra, P. Saha, T. Punniyamurthy, J. Org. Chem. 74 (2009) 1971–1976.
[32] L. Rout, S. Jammi, T. Punniyamurthy, Org. Lett. 9 (2007) 3397–3399.
[33] N.V. Suramwar, S.R. Thakare, N.N. Karade, N.T. Khaty, J. Mol. Catal. A: Chem. 359 (2012) 28-34.
[34] J. Safaei-Ghomi, M. A. Ghasemzadeh, J. Nano Struct. 1 (2012) 243-248.
[35] G.R. Chaudhary, P. Bansal, N. Kaur, S.K. Mehta, RSC Adv. 14 (2014) 49462-49470.
[36] P.K. Chaudhari, S. Chand, I.M. Mishra, Chem. Eng. Commun. 199 (2012) 874–888.
[37] S. Golchin, M.H. Mosslemin, A. Yazdani-Elah-Abadi, N. Shams, Res. Chem. Intermed. 43 (2017) 1735-1749.
