Silica-bonded n-propyldiethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of coumarin and biscoumarin derivatives

Document Type: Articles

Authors

1 Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran.

2 Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.

3 Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.

Abstract

Silica-bonded n-propyldiethylenetriamine sulfamic acid (SBPDSA) was found as an efficient solid acid for the synthesis of coumarins. Coumarin derivatives were obtained via the Pechmann condensation reaction of phenols and β-keto-esters at 80 oC under solvent-free conditions. Also, biscoumarins were obtained via the condensation of aldehydes and 4-hydroxycoumarin in water at reflux conditions. The heterogeneous solid acid showed much the same efficiency when used in consecutive reaction runs.

Keywords


[1] R.D.H. Murray, J. Mendez, S.A. Brown, The Natural Coumarins Occurrence Chemistry and Biochemistry Wiley and Sons, New York, 1982.
[2] R.O. O’Kennedy, R.D. Zhorenes, Coumarins: Biology Applications and Mode of Action John Wiley and Sons, Chichester, 1997.
[3] I. Kempen, D. Papapostolou, N. Thierry, L. Pochet, S. Counerotte, B. Masereel, J.M. Foidart, M.J. Reboud-Ravaux, A. Noel, B. Pirotte, Br. J. Cancer 88 (2003) 1111-1118.
[4] C. Kontogiorgis, D. Hadjipavlou-Litina, J. Enz. Inhib. Med. Chem. 18 (2003) 63-69.
[5] C. Spino, M. Dodier, S. Sotheeswaran, Bioorg. Med. Chem. Lett. 8 (1998) 3475-3478.
[6] E. Quezada, G. Delogu, C. Picciau, L. Santana, G. Podda, F. Borges, V. Garcia-Moraes, D. Vina, F. Orallo, Molecules 15 (2010) 270-279.
[7] S. Vilar, E. Quezada, L. Santana, E. Uriarte, M. Yanez, N. Fraiz, C. Alcaide, E. Cano, F. Orallo, Bioorg. Med. Chem. Lett. 16 (2006) 257-261.
[8] M. Zabradink, The Production and Application of Fluorescent Brightening Agent John Wiley and Sons, New York, 1992.
[9] D.P. Specht, P.A. Martic, S. Farid, Tetrahedron 38 (1982) 1203-1211.
[10] W.C. Meuly, Kirk-Othmer Encyclopedia of Chemical Technology 3rd ed, Vol 7, John Wiley and Sons, New York, 1979, 196-206.
[11] H.V. Pechmann, E. Hanke, Chem. Ber. 34 (1901) 354-362.
[12] B.M. Reddy, M. Patil, P. Lakshmanan, J. Mol. Catal. A: Chem. 256 (2006) 290-294.
[13] J.K. Augustine, A. Bombrun, B. Ramappa, C. Boodappa, Tetrahedron Lett. 53 (2012) 4422-4425.
[14] P.K. Singh, D.U. Singh, S.D. Samant, Synlett (2004) 1909-1912.
[15] H. Valizadeh, A. Shockravi, Tetrahedron Lett. 46 (2005) 3501-3503.
[16] S.B. Patil, R.P. Bhat, V.P. Raje, S.D. Samant, Synth. Commun. 36 (2006) 525-531.
[17] K. Jung, Y.J. Park, J.S. Ryu, Synth. Commun. 38 (2008) 4395-4406.
[18] B.C. Raju, T.H. Babu, J.M. Rao, Indian J. Chem. 48 B (2009) 120-123.
[19] E.A. Gunnewegh, A.J. Hoefnegal, H. Van Bekkum, J. Mol. Catal. A: Chem. 100 (1995) 87-92.
[20] J.C. Rodriguez-Dominguez, G. Kirsch, Tetrahedron Lett. 47 (2006) 3279-3281.
[21] M. Dabiri, P. Salehi, M.A. Zolfigol, M. Baghbanzadeh, Heterocycles 71 (2007) 677-682.
[22] J. Azizian, A.A. Mohammadi, I. Bidar, P. Mirzaei, Monatsh. Chem. 139 (2008) 805-808.
[23] B. Karimi, D. Zareyee, Org. Lett. 10 (2008) 3989-3992.
[24] K. Niknam, D. Saberi, M. Baghernejad, Chin. Chem. Lett. 20 (2009) 1444-1448.
[25] A. Sinhamahapatra, N. Sutradhar, S. Pahari, H.C. Bajaj, A.B. Panda, Appl. Catal. A: Gen. 394 (2011) 93-100.
[26] S. Ghodke, U. Chudasama, Appl. Catal. A: Gen. 453 (2013) 219-226.
[27] M. Nouri Sefat, A. Deris, K. Niknam, Chin. J. Chem. 29 (2011) 2361-2367.
[28] T. Rahi, M. Baghernejad, K. Niknam, Chin. J. Catal. 33 (2012) 1095-1100.
[29] K. Niknam, A. Deris, F. Naeimi, F. Majleci, Tetrahedron Lett. 52 (2011) 4642-4645.
[30] T. Rahi, M. Baghernejad, K. Niknam, Chin. Chem. Lett. 23 (2012) 1103-1106.
[31] F. Rohandeh, D. Saberi, K. Niknam, Iran. J. Catal. 1 (2011) 71-78.
[32] S. Tayebi, K. Niknam, Iran. J. Catal. 2 (2012) 69-74.
[33] K. Niknam, A. Jamali, M. Tajaddod, A. Deris, Chin. J. Catal. 33 (2012) 1312-1317.
[34] H. Tajik, K. Niknam, S. Karimian, Iran. J. Catal. 3 (2013) 107-113.
[35] S. Ghasemi, M. Baghernejad, K. Niknam, Iran. J. Catal. 3 (2013) 165-169.
[36] M. Makvandi, F. Abiar Dil, A. Malekzadeh, M. Baghernejad, K. Niknam, Iran. J. Catal. 3 (2013) 221-228.
[37] H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7 (2010) 890-894.
[38] A. Davoodnia, Bull. Korean Chem. Soc. 32 (2011) 4286-4290.
[39] J.M. Khurana, S. Kumar, Tetrahedron Lett. 50 (2009) 4125-4127.
[40] S. Qadir, A. Ahmad Dar, K. Zaman Khan, Synth. Commun. 38 (2008) 3490-3499.
[41] M. Kidwi, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268 (2007) 76-81.
[42] G.X. Gong, J.F. Zhou, L.T. An, X.L. Duan, S.J. Ji, Synth. Commun. 39 (2009) 497-505.
[43] K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A.U. Rahman, S. Perveen, Bioorg. Med. Chem. 12 (2004) 1963-1968.