Multi-component, one-pot, aqueous media preparation of dihydropyrano[3, 2-c]chromene derivatives over MgO nanoplates as an efficient catalyst

Document Type: Articles

Authors

1 Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, P.O. Box: 517; Najafabad, Esfahan, Iran.

2 Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College, Melvisharam – 632 509, Tamil Nadu, India.

Abstract

Red pine leafs were applied for the green method preparation of MgO nano-plates. The MgO nano-plates were used for the one-pot synthesis of dihydropyrano [3,2-c] chromene derivatives. This procedure is very simple and affords excellent yields. MgO nanoplates were synthesized via a simple precipitation method with the using of an extract solution of red pine leaves. The XRD pattern shows a cubic phase ofMgO . Field Emission Scanning Electronic Microscopy (FE-SEM) shows clearly that the surface of the as-prepared MgO nano-plates have a homogeneous microstructure made up of layers of various sizes and forms. The plates form irregular grains with a lateral size of 40-110 nm.

Keywords


[1] G.R. Green, J.M. Evans, A.K. Vong, In Comprehensive Heterocyclic Chemistry II; A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Eds.; Pergamon: Oxford, 1995; Vol. 5; p. 469.
[2] G.P. Ellis, The Chemistry of Heterocyclic Compounds Chromenes, chap. II., in, Chromanes and Chromones, ed., A. Weissberger and E.C. Taylor, Wiley, New York, 1997, 11.
[3] E.A. Hafez, M.H. Elnagdi, A.A. Elagamey, F.A.M. El-Taweel, Heterocycles 26 (1987) 903-907.
[4] M.A. Sofan, F.M.A. El-Taweel, M.H. Elnagdi, Liebigs Ann. Chem. (1989) 935-936.
[5] F.M. Abdel Galil, B.Y. Riad, S.M. Sherif, M.H. Elnagdi, Chem. Lett. (1982) 1123-1126.
[6] R.S. Varma, R. Dahiya, J. Org. Chem. 63 (1998) 8038-8041.
[7] M.M. Khafagy, A.H.F. Abd El-Wahab, F.A. Eid, A.M. El-Agrody, Farmaco, 57 (2002) 715-722.
[8] S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35 (1975) 3750-3754.
[9] D.R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, S. Liu, A. Sambandam, P.A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 15 (2005) 1587-1590.
[10] G. Bianchi, A. Tava, Agr. Biol. Chem. Tokyo 51 (1987) 2001-2002.
[11] F. Eiden, F. Denk, Arch. Pharm. 324 (1991) 353-354.
[12] A.G.A. Elagemey, F.M.A.A. El-Taweel, M.N.M. Khodeir, M.H. Elnagdi, Bull. Chem. Soc. Jpn. 66 (1993) 464-468.
[13] R. Maggi, A. Mazzacanni, P. Righi, G. Sartori, Tetrahedron 57 (2001) 1395-1398.
[14] T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, X.R. Song, Synlett (2003) 2001-2004.
[15] A.-Q. Zhang, M. Zhang, H.-H. Chen, J. Chen, H.-Y. Chen, Synth. Commun. 37 (2007) 231-235.
[16] M. Kidwai, S. Saxena, M.K. Rahman Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15 (2005) 4295-4298.
[17] N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35 (2014) 391-395.
[18] B.S. Kumar, N. Srinivasulu, R.H. Udupi, B. Rajitha, Y.T. Reddy, P.N. Reddy, P.S. Kumar, J. Heterocycl. Chem. 43 (2006) 1691-1693.
[19] G. Shanthi, P.T. Perumal, Tetrahedron Lett. 48 (2007) 6785-6789.
[20] M.M. Heravi, K. Bakhtiari, V. Zadsirjan, F.F. Bamoharram, O.M. Heravi, Bioorg. Med. Chem. Lett. 17 (2007) 4262-4265.
[21] A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A.H. Rezayan, A. Sarvary, S. Weng Ng, J. Comb. Chem. 11 (2009) 956-959.
[22] K. Niknam, A. Jamali, Chin. J. Catal. 33 (2012) 1840-1849.
[23] J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
[24] A. Solhy, A. Elmakssoudi, R. Tahir, M. Karkouri, M. Larzek, M. Bousmina, M. Zahouily, Green Chem. 12 (2010) 2261–2267.
[25] M. Ghashang, M. Kargar, M.R.M. Shafiee, S.S. Mansoor, A. Fazlinia, H. Esfandiari, Rec. Pat. Nanotech. 9 (2015) 204-211.