Nano-peanut shell-OSO3H: Green and natural-based renewable nanocatalyst for one-pot synthesis of dihydropyrano[3,2-b]chromenedione derivatives
محورهای موضوعی : Iranian Journal of CatalysisBahareh Sadeghi 1 , Zahra Lasemi 2 , Mansooreh Pisheh Abadi 3
1 - Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran
2 - Department of Chemistry, Firoozkooh Branch, Islamic Azad University, Firoozkooh, Iran.
3 - Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran.
کلید واژه: Kojic acid, Nano-peanut shell‑OSO3H, Dihydropyrano[3, 2-b]chromenedione, Green nanocatalyst,
چکیده مقاله :
Nano-peanut shell‑OSO3H nanoparticles were simply prepared and characterized by the scanning electron microscopy (SEM), transmission electron microscope (TEM), fourier transform infrared (FT-IR), energy dispersive X-ray spectroscopy (EDX), and thermal analysis techniques (TGA/DTG). The catalytic activity of nano-peanut shell‑OSO3H was studied in the synthesis of biologically important 4H-pyran derivatives. The reaction involves the use of Kojic acid, 5,5-dimethyl-1,3-cyclohexanedione, and various benzaldehydes. A wide range of benzaldehydes is compatible in this reaction, producing excellent yields in a short time. The successful synthesis of dihydropyrano[3,2-b]chromenedione derivatives shows that nano-peanut shell‑OSO3H has high catalytic activity and can be effectively used as a green catalyst.
[1] C.C.A. Cariou, G.J. Clarkson, M. Shipman, J. Org. Chem. 73 (2008) 9762–9764.
[2] S.M. Kupchan, Y. Komoda, W.A. Court, G.J. Thomas, R.M. Smith, A. Karim, C.J. Gilmore, R.C. Haltiwanger, R.F. Bryan, J. Am. Chem. Soc. 94 (1972) 1354–1356.
[3] C. Mukhopadhyay, A. Datta, R.J. Butcher, Tetrahedron Lett. 50 (2009) 4246–4250.
[4] C. Mukhopadhyay, P.K. Tapaswi, M.G.B. Drew, Tetrahedron Lett. 51 (2010) 3944–3950.
[5] L. Weber, K. Illgen, M. Almstetter, Synlett (1999) 366–374.
[6] A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova, D.H. Evans, Org. Lett. 4 (2002) 423–425.
[7] L. Weber, Curr. Med. Chem. 9 (2002) 2085–2093.
[8] M.P. Zhu, I. Kimiaki, Tetrahedron Lett. 38 (1997) 5301–5302.
[9] X. Xiong, M.C. Pirrung, Org. Lett. 10 (2008) 1151–1154.
[10] K. Nakajima, M. Hara, ACS Catal. 2 (2012) 1296–1304.
[11] T. Okuhara, Chem. Rev. 102 (2002) 3641–3666.
[12] W. Zhao, B. Yang, CH. Yi, Z. Lei, J. Xu, Ind. Eng. Chem. Res. 49 (2010) 12399–12404.
[13] Y. Wu, B. Li, J.F. Hu, J.N. Chen, X.S. Zheng, L.B. Wen, Petrochem. Technol. 38 (2009) 240–243.
[14] D. Zeng, S. Liu, W. Gong, G. Wang, J. Qiu, H. Chen, Appl. Catal. A 469 (2014) 284–289.
[15] B.V.S. Reddy, M.R. Reddy, G. Narasimhulu, J.S. Yadav, Tetrahedron Lett. 51 (2010) 5677–5679.
[16] W.L. Li, L.Q. Wu, F.L. Yan, J. Braz. Chem. Soc. 22 (2011) 2202–2205.
[17] W.L. Li, J.Y. Liang, T.B. Wang, Y.Q. Yang, Collect. Czech. Chem. Commun. 76 (2012) 1791–1797.
[18] Y. Li, X. Meng, G. Cai, B. Du, B. Zhao, Res. Chem. Intermed. 40 (2014) 699–709.
[19] B. Sadeghi, A. Namakkoubi, A. Hassanabadi, J. Chem. Res. 37 (2013) 11–13.
[20] B. Sadeghi, M. Shirkhani, A. Hassanabadi, J. Chem. Res. 39 (2015) 112–114.
[21] B. Sadeghi, A. Hassanabadi, E. Taghvatalab, J. Chem. Res. 35 (2011) 707–708.
[22] B. Sadeghi, M. Bouslic, M.R. Shishehbore, J. Iran. Chem. Soc. 12 (2015) 1801–1808.
[23] B. Sadeghi, M. Ghasemi Pirbaluti, P. Farokhi Nezhad, R. Abbasi Nezhad, Res. Chem. Intermed. 41 (2015) 4047–4055.
[24] B. Sadeghi, P. Farokhi Nezhad, S. Hashemian, J. Chem. Res. 38 (2014) 54–57.
[25] Z. Lasemi, B. Sadeghi, F. Amiri Tavasoli, Iran. J. Catal. 6 (2016) 51–55.
[26] G. Zhang, Y. Qu, J. Chem. (2013) 1-4.
[27] S. Pourshahrestani, I. Mohammadpoor‑Baltork, M. Moghadam, S. Tangestaninejad, A. R. Khosropour, V. Mirkhani, J. Iran. Chem. Soc. 12 (2015) 573-580.
[28] M. Zirak, M. Azinfar, M. Khalili, Curr. Chem. Lett. 6 (2017) 105–116.
[29] E. Estakhri, M. Nasr-Esfahani, I. Mohammadpoor‐Baltork, S. Tangestaninejad, M. Moghadam, V. Mirkhani, Appl. Organomet. Chem. 31 (2017) e3799.
