Document Type: Original Research Article

Author

Department of Chemistry, College of Sciences, University of Birjand, P. O. Box 97175-615, Birjand, Iran

Abstract

In this research, (Carboxy-3-oxopropylamino)-3-propylsilylcellulose (COPAPSC) as an organocatalyst, has been synthesized by grafting of succinic anhydride on the NH2-modified cellulose (cellulose functionalized with 3- aminopropyltriethoxysilane). The –CO2H group-functionalized cellulose (COPAPSC) is used as a catalyst for the synthesis of coumarin derivatives from the reaction of phenolic substrate and β- Keto-esters under solvent-free conditions. The results showed that the yield of products is between 85-94%. The advantages of this reaction include simple work-up, short reaction time, excellent yields as well as easily separation of catalyst. The catalyst can be reused several times in subsequent reactions without any decreasing in the catalyst reactivity.

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[1] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev., 2011, 111, 3036–3075.

[2] S.E. Garc´ıa-Garrido, J. Francos, V. Cadierno, J.M. Basset V. Polshettiwar, Chem. Sus. Chem., 2011, 4, 104–111.

[3] (a) H.U. Blaser, A. Baiker, R. Prins, Heterogeneous catalysis and fine chemicals IV, Elsevier, Netherlands, 1997; (b) J.M. Thomas and W.J. Thomas, Principles and practice of heterogeneous catalysis, VCH, Weinheim, 1997.

[4] N. Audic, H. Clavier, M. Mauduit, J.C. Guillemin, J. Am. Chem. Soc., 2003, 125, 9248–9249.

[5] (a) L.J. Gu, D. Ma, S.D. Yao, C.L. Wang, W.J. Shen, X.H. Bao, Chem. Commun., 2010, 46, 1733–1735; (b) M. Iwasaki, H. Shinjoh, Chem. Commun., 2011, 47, 3966–3968.

[6] E. Ortel, S. Sokolov, C. Zielke, L. Lauermann, S. Selve, K. Weh, B. Paul, J. Polte and R. Kraehnert, Chem. Mater., 2012, 24, 3828–3838.

[7] M. Yang, M. Zhou, A.H. Zhang, C.

Zhang, J. Phys. Chem. C, 2012, 116,

22336–22340.

[8] R.B.N. Baig, R.S. Varma, Chem. Commun., 2012, 48, 2582–2584.

[9] R.B.N. Baig, R.S. Varma, Green Chem., 2013, 15, 1839–1843.

[10] H. Firouzabadi, N. Iranpoor, A. Ghaderi, Org. Biomol. Chem., 2011, 9, 865–871

[11] R.S. Verma, S.L. Jain, B. Sain, Chem. Cat. Chem., 2011, 3, 1329–1332.

[12] E. Guibal, Prog. Polym. Sci., 2005, 30, 71–109.

[13] M.Chtchigrovsky, Y. Lin, K. Ouchaou, M. Chaumontet, M. Robitzer, F. Quignard, F. Taran, Chem. Mater, 2012, 24, 1505–1510.

[14] H.Y. Yu, G.Y. Chen, Y.B. Wang, J.M. Yao, Cellulose, 2015, 22, 261–273.

[15] R.O. Kennedy, R.D. Thornes, Coumarins: Biology, Applications and Mode of Action, John Wiley and Sons, Chichester, 1997.

[16] O. Snow, Amphetamine syntheses, Psychoactive Synth. Ser.: USA 1, 1998.

[17] S.M. Sethna, N.M. Shah, Chem. Rev. 1945, 36, 1–62.

[18] X.T. Liang, W.S. Fang, Medicinal chemistry of bioactive natural products, John Wiley & Sons: Hoboken, New Jersey, 2006.

[19] G. Cavettos, G.M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron-Asymmetry, 2001, 12, 707–709.

[20] V.H Pechmann, C. Duisberg, Chem. Ber., 1884, 17, 929-979.

[21] G. Brufola, F. Fringuelli, O. Piematti, F. Pizzo, Heterocycles, 1996, 43, 1257-1266.

[22] N.Cairns, M.L. Harwood, D.P Astles, J. Chem. Soc. Perkin Trans, 1994, 1, 3101-3107.

[23] I. Yavari, R.R Hekmat-shoa, A. Zonouzi, Tetrahedron Lett., 1998, 39, 2391-2392.

[24] J.R. Johnson, Org. React., 1942, 1, 210-265.

[25] R.L Shriner, Org. React., 1942, 1, 1-37.

[26] L.L. Woods, J. Sapp, J. Org. Chem., 1962, 27, 3703-3705.

[27] F.W. Canter, F.H. Curd, A. Robertson, J. Chem. Soc. CLXVI.-Hydroxy-carbonyl compounds, Part III, 1931, 1255-1265.

[28] H. Valizadeh, A. Shockravi, Tetrahedron Lett., 2005, 46, 3501-3503.

[29] P. Sun, Z. Hu, Synth. Commun., 2005, 35, 1875-1880.

[30] S.K. De, R.A. Gibbs, Synthesis, 2005, 8, 1231–1233.

 [31] V. M. Alexander, R. P. Bhat, S. D. Samant, Tetrahedron Letters, 2004, 45, 7999–8001.

[32] S. S. Bahekar, D. B. Shinde, Tetrahedron Letters, 2005, 46, 6957–6959.

[33] E.V.O. John, S.S. Israelstam, J. Org. Chem., 1961, 26, 240–242.

[34] T.S. Li, Z.H. Zhang, F. Yang, C.G. Fu, J. Chem. Res., 1998, 38–39.

[35] M.C. Laufer, H. Hausmann, W.F. Hölderich, J. Catal., 2003, 218, 315–320.

[36] R. Sabou, W.F. Hoelderich, D. Ramprasad, R. Weinand, J. Catal., 2005, 232, 34–37.

[37] B. Karimi, H. Behzadnia, Catalysis Communications, 2011, 12, 1432–1436.

[38] B. Tyagi, M.K. Mishra, R.V. Jasra, J. Mol. Catal. A: Chem., 2007, 276, 47–56.

[39] S. Selvakumar, M. Chidambaram, A.P. Singh, Catal. Commun., 2007, 8, 777–783. 

[40] B. Karimi, D. Zareyee, Organic Leeters, 2008, 10, 3989-3992.

[41] M. Dabiri, M. Baghbanzadeh, S. Kiani, Y. Vakilzadeh, Monatshefte fur Chemie, 2007, 138, 997–999.

[42] M. Mokhtary, F. Najafizadeh, C. R. Chimie, 2012, 15, 530–532.

[43] S. Palaniappan, R. C.Shekhar, Journal of Molecular Catalysis A: Chemical, 2004, 209, 117–124.

[44] A. Sinhamahapatra, N. Sutradhar, S. Pahari, H.C. Bajaj, A. B. Panda, Applied Catalysis A: General, 2011,394, 93–100.

[45] M.A. Nasseri, M. Salimi, Letters in Organic Chemistry, 2013, 10, 164-170.

[46] M.A. Nasseri, A. Mohammadinezhad, M. Salimi J. Iran, Chem. Soc., 2015, 12, 81–86.

[47] A. Mohammadinezhad, M.A. Nasseri, M. Salimi, RSC Adv., 2014, 4, 39870–39874.

[48] M.A. Nasseri, M. Salimi, A.A. Esmaeili, RSC Adv., 2014, 4, 61193–61199.

[49] M. Salimi, M.A. Nasseri, T. Daliran Chapesshloo, B. Zakerinasab, RSC Adv., 2015, 5, 33974-33980.