An efficient solvent-free synthesis of 1,8-dioxo-octahydroxanthenes by using Fe2(SO4)3.7H2O as catalyst

Khoeiniha, Reyhaneh; Ezabadi, Ali; Olyaei, Abolfazl

Document Type : Original Research Article

Authors

¹ Department of Chemistry, Faculty of Sciences, Central Tehran Branch, Islamic Azad University, P.O. BOX 14676-86831,Tehran, Iran

² Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran.

Abstract

A facile and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes has been developed by one-pot Knoevenagel condensation, Michael addition and cyclodehydration reaction of dimedone (active methylene carbonyl compound) with aromatic aldehydes in the presence of Iron (III) sulfate hydrate as a solid acidic catalyst under solvent-free conditions. Various aromatic aldehydes were utilized in the reaction and in all situations the desired product were synthesized successfully. The present methodology is cost-effective in addition to other advantages like high yields of products in shorter reaction time and simple workup procedure. The non toxicity and easy availability of the catalyst makes this protocol efficient and environmentally benign.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G.J. Thomas, PCT Int. Appl. WO 9706178; Chem. Abstr., 1997, 126, p212377y.

[2] T. Hideo, Tokkyo Koho JP 56005480; Chem. Abstr., 1981, 95, 80922b.

[3] R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta. Biochim. Pol., 1998, 45, 833-845.

[4] S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, D. Sun, B.B. Rosenblum, S.H. Khan, M.U.S. Taing, Patent, US 6583168; Chem. Abstr., 2003, 139, p54287f.

[5] A. Banerjee, A.K. Mukherjee, Stain Technol., 1981, 56, 83-85.

[6] O. Sirkencioglu, N. Talinli, A. Akar, J. Chem. Res. (S), 1995, 502-506.

[7] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, J. Appl. Phys., 2002, 35, 1473-1476.

[8] C.G. Knight, T. Stephens, Biochem. J., 1989, 258, 683-687.

[9] A. Arnone, L. Merlini, G. Nasini, Tetrahedron Lett., 1972, 3503-3506.

[10] B. Ravindranath, T.R. Sheshadri, Phytochemistry, 1973, 12, 2781-2788.

[11] J. Kinjo, H. Uemura, T. Nohara, M. Yamashita, N. Marubayashi, K. Yoshihira, Tetrahedron Lett., 1995, 36, 5599-5602.

[12] A. Bekaert, J. Andrieux, M. Plat, Tetrahedron Lett., 1992, 33, 2805-2806.

[13] R.J. Sarma, J.B. Baruah, J. Org. Chem., 1943, 8, 316-319.

[14] D.W. Knight, P.B. Little, Synlett, 1998, 1141-1143.

[15] D.W. Knight, P.B. Little, J. Chem. Soc. Perk. T., 2001, 115, 1771-1777.

[16] A. Jha, J. Beal, Tetrahedron Lett., 2004, 45, 8999-9001.

[17] C.W. Kuo, J.M. Fang, Synth. Commun., 2001, 31, 877-892.

[18] T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang, T.S. Li, Synlett, 2004, 866-870.

[19] B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A Chem., 2006, 247, 233-239.

[20] G. Song, B. Wang, H. Luo, L. Yang, Catal. Commun., 2007, 8, 673-676.

[21] B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth, L. Nagarapu, Catal. Commun., 2007, 8, 535-538.

[22] P. Srihari, S.S. Mandal, J.S.S. Reddy, R. Srinivasa Rao, J.S. Yadav, Chin. Chem. Lett., 2008, 19, 771-774.

[23] G.H. Mahdavinia, M.A. Bigdeli, Y.S. Hayeniaz, Chin. Chem. Lett., 2009, 20, 539-541.

[24] M. Bigdeli, Chin. Chem. Lett., 2010, 21, 1180-1182.

[25] S. Samantaray, P. Kar, G. Hota, B.G. Mishra, Ind. Eng. Chem. Res., 2013, 52, 5862-5870.

[26] M. Nasr-Esfahani, T. Abdizadeh, J. Chem. Sci. Technol., 2013, 2, 14-20.

[27] K. Tanaka, F. Toda, Chem. Rev., 2000, 100, 1025-1074.

[28] L.J. Li, X.Y. Zhang, G.S. Zhang, Chin. Chem. Lett., 2004, 15, 508-511.

[29] M.T. Maghsoodlou, S.M. Habibi-Khorassani, Z. Shahkarami, N. Maleki, M. Rostamizadeh, Chin. Chem. Lett., 2010, 21, 686-689.

[30] S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A: Chem., 2007, 269, 53-57.

[31] A. John, P.J.P. Yadav, S. Palaniappan, J. Mol. Catal. A: Chem., 2006, 248, 121-125.

[32] X. Fan, X. Hu, X. Zhang, J. Wang, Can. J. Chem., 2005, 83, 16-20.

[33] G.H. Mahdavinia, J. Iran. Chem. Res., 2008, 1, 11-17.

[34] H.N. Karade, M. Sathe, M.P. Kaushik, ARKIVOC(xiii), 2007, 252-258.

[35] G. Karthikeyan, A. Pandurangan, J. Mol. Catal. A: Chem., 2009, 311, 36-45.

Iranian chemical communication

An efficient solvent-free synthesis of 1,8-dioxo-octahydroxanthenes by using Fe2(SO4)3.7H2O as catalyst

References

References

[28] L.J. Li, X.Y. Zhang, G.S. Zhang, Chin. Chem. Lett., 2004, 15, 508-511.

Volume 4, Issue 3, pp. 236-358, Serial No. 12
July 2016
Pages 273-282

An efficient solvent-free synthesis of 1,8-dioxo-octahydroxanthenes by using Fe2(SO4)3.7H2O as catalyst

References

References

[28] L.J. Li, X.Y. Zhang, G.S. Zhang, Chin. Chem. Lett., 2004, 15, 508-511.

Volume 4, Issue 3, pp. 236-358, Serial No. 12July 2016Pages 273-282

Volume 4, Issue 3, pp. 236-358, Serial No. 12
July 2016
Pages 273-282