Nano silica sulfuric acid catalyzed synthesis of 2-substituted aryl (indolyl) kojic acid derivatives

Document Type: Articles

Authors

1 Department of Chemistry, Firoozkooh branch, Islamic Azad University, Firoozkooh, Iran.

2 Department of Chemistry, Islamic Azad University, Yazd Branch, P.O.Box 89195-155, Yazd, Iran

Abstract

Nano silica sulfuric acid as a solid acid, was described to be an effective catalyst for one-pot three-component reaction of kojic acid, aryl aldehydes and indoles for the preparation of 2-substituted aryl (indolyl) kojic acid derivatives. The catalyst was prepared by combination of chlorosulfonic acid to nano silica gel. The size of nanoparticles were observed with SEM.All prepared compounds with melting points, 1H NMR and 13C NMR were characterized. High yields, simple operation, easy-work procedure, mild reaction conditions are some advantages of this protocol. The present method does not involve any hazardous organic solvent. Therefore, this procedure could be classified as green chemistry.

Keywords


[1] (a) R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29 (1996) 123-131. (b) N.K. Terret, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steel, Tetrahedron 51 (1995) 8135-8173. (c) A. Domling, Chem. Rev. 106 (2006) 17-89.
[2] G.W. Gribble, J. Chem. Soc. Perkin Trans 1. (2000) 1045-1076.
[3] W.N. Xiong, C.G. Yang, B. Jiang, Bioorg. Med. Chem. 9 (2001) 1773-1780.
[4] S. Zhu, S. Ji, X. Su, C. Sun, Y. Liu, Tetrahedron Lett. 49 (2008) 1777-1781.
[5] S.S. El-Nakkady, S.E.S. Abbas, H.M. Roaiah, I.H. Ali, Global. J. Pharm. 6 (2012) 166-177.
[6] L.H. Franco, E.B.K. Joffe, L. Puricelly, M. Tatian, A.M. Seldes, J.A. Palermo, J. Nat. Prod. 61 (1998) 1130-1132.
[7] S. Zhu, S. Ji, K. Zhao, Y. Liu, Tetrahedron Lett. 49 (2008) 2578-2582.
[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] (a) M. Sefkow, H. Kaatz, Tetrahedron Lett. 40 (1999) 6561-6562. (b) H.N. Barham, G.N. Reed, J. Am. Chem. Soc. 60 (1938) 1541-1545.
[11] (a) Y. Kobayashi, H. Kayahara, K. Tadasa, H. Tanaka, Bioorg. Med. Chem. Lett. 6 (1996) 1303-1308. (b) R.C. Fox, P.D. Taylor, Synth. Commun. 28 (1998) 1575-1583. (c) A.A. Shestopalov, L.A. Rodinovskaya, A.M. Shestopalov, V.P. Litvinov, Russ. Chem. Bull. 53 (2004) 724-725.
[12] B.V.S. Reddy, M.R. Reddy, Ch. Madan, K.P. Kumar, M.S. Rao, Bioorg. Med. Chem. Lett. 20 (2010) 7507-7511.
[13] B. Sadeghi, Z. Lasemi, F. Amiri Tavasoli, S. Hashemian, H. Zahedi, Syn. React. Inorg. Met. 44 (2014) 1497-1503.
[14] B. Sadeghi, A. Hassanabadi, S. Bidaki, J. Chem. Res. 35 (2011) 666-668. (b) B. Sadeghi, T. Ziya, J. Chem. (2013) Article ID 179013, 5 pages
[15] (a) B. Sadeghi, P.F. Nezhad, S. Hashemian, J. Chem. Res. 38 (2014) 54-57. (b) B. Sadeghi, M. Ghasemi Pirbaluti, P. Farokhi Nezhad, R. Abbasi Nezhad, Res. Chem. Intermed. 41 (2013) 4047-4055.