Synthesis of dihydrofurans using biosynthesized CuO nanoparticles

Iranian Journal of Catalysis

مقاله 3، دوره 8، شماره 4، اسفند 2018، صفحه 257-262   

نوع مقاله: Articles

نویسندگان

Javad Safaei-Ghomi^{* 1}؛ Hossein Shahbazi-Alavi²

¹Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 51167, I. R. Iran.

²Young Researchers and Elite Club, Kashan Branch, Islamic Azad University, Kashan, Iran.

چکیده

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.

کلیدواژه‌ها

Dihydrofurans؛ Reusable catalyst؛ Biosynthesized CuO nanoparticles؛ Green synthesis؛ One-pot

مراجع

[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.