Melamine trisulfonic acid: A new, efficient and reusable catalyst for the protection of alcohols, phenols, aldehydes and amines
الموضوعات : Iranian Journal of CatalysisFarhad Shirini 1 , Mohammad A. Zolfigol 2 , Jalal Albadi 3 , Toktam F. Rastegar 4
1 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
2 - College of Chemistry, Bu-Ali Sina University, Hamedan,I.R. Iran
3 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
4 - College of Chemistry, Bu-Ali Sina University, Hamedan,I.R. Iran
الکلمات المفتاحية: Alcohols, Aldehydes, Melamine trisulfonic acid, Phenols, amine,
ملخص المقالة :
Tetrahydropyranylation of alcohols and phenols, acetylation of aldehydes and N-Boc protection of amines are efficiently catalyzed by melamine trisulfonic acid (MTSA). All reactions were performed at room temperature in good to high yields.
[1] L.F. Fieser, M. Fieser, Reagents for Organic Synthesis, John Wiley and Sons Inc., New York, 1999.
[2] M. Miyashita, A. Yoshikoshi, P.A. Grieco, J. Org. Chem. 42 (1977) 3772-3774.
[3] F. Chavez, R. Godinez, Synth. Commun. 22 (1992) 159-164.
[4] D.M. Pore, U.V. Desai, R.B. Mane, P.P. Wadgaonkar, Synth. Commun. 34 (2004) 2135-2142.
[5] B. Karimi, J. Maleki, Tetrahedron Lett. 43 (2002) 5353-5355.
[6] M.M. Heravi, F.K. Behbahani , H.A. Oskooie, R. Hekmat Shoar, Tetrahedron Lett. 46 (2005) 2543-2548.
[7] H. Firouzabadi, N. Iranpoor , H. Hazarkhani, Synth. Commun. 34 (2004) 3623-3630.
[8] B. Karimi, M. Khalkhali, J. Mol. Catal. A: Chem. 232 (2005) 113-117.
[9] F. Shirini, K. Marjani, H. Taherpour Nahzomi, Phosphorus, Sulfur, Silicon 182 (2007) 2235-2240.
[10] M. Wang, Z.G. Song, H. Jiang, H. Gong, Monatsh. Chem. 138 (2007) 599-602.
[11] M.J. Gregory, J. Chem. Soc. (1970) 1201-1207.
[12] J.G.Jr. Frick, R.J.Jr. Harper, J. Appl. Polymer Sci. 29 (1984) 1433- 1447.
[13] W.R. Eanderson, Eur. Pat. Apll. EP. (1985, 125, 781; Chem. Abstr. 102, P64010K), 1985.
[14] J.S. Yadav, B.V.S. Reddy, G.S.K.K. Reddy, Tetrahedron Lett. 41 (2000) 2695-2697.
[15] F. Freeman, E.M. Karchefski, J. Chem. Eng. Data 22 (1997) 355-357.
[16] J.K. Michie, J.A. Miller, Synthesis (1981) 824-825.
[17] B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett (2000) 623-624.
[18] G. Smitha, Ch.S. Reddy, Tetrahedron 59 (2003) 9571-9576.
[19] X.Y. Zhang, L.J. Li, G.S. Zhang, Green Chem. 5 (2003) 646-649.
[20] C. Wang, M. Li, Synth. Commun. 32 (2002) 3469-3473.
[21] K. Manjula, M. Afzal Pasha, Synth. Commun. 37 (2007) 1563-1569.
[22] A.K. Bhattacharya, M. Mujahid, A.A. Natu, Synth. Commun. 38 (2008) 128-134.
[23] V.T. Kamble, V.S. Jamode, N.S. Joshi, A.V. Biradar, R.Y. Deshmukh, Tetrahedron Lett. 47 (2006) 5573-5576.
[24] H. Wu, Y. Shen, L.Y. Fan, Y. Wan, D. Shi, Tetrahedron 62 (2006) 7995-7998.
[25] U.Y. Desai, T.S. Thopta, D.M. Pore, P.P. Wadgaonkar, Catal. Commun. 7 (2006) 508-511.
[26] M. Wang, H. Gong, H. Jiang, Z. Wang, Synth. Commun. 36 (2006) 1953-1960.
[27] A.V. Reddy, K. Ravinder, V.L.N. Reddy, V. Ravikanth, Y. Venkateswarlu, Synth. Commun. 33 (2003) 1531-1536.
[28] C. Lutz, V. Lutz, P. Knochel, Tetrahedron 54 (1998) 6385-6402.
[29] T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Chemistry, John Wiley and Sons Inc., New York, 1999.
[30] P.J. Kocienski, Protecting Groups, George Thieme Verlag, Stuttgart, New York, 2000.
[31] E. Wuensch, E. Muller, O. Bayer, H. Meerwein, K. Ziegle, Methods of Organic Chemistry, 4 th ed. Houben-Weyl George Thieme Verlag, Stuttgat, Vol 15 / 1, 1974.
[32] E. Gross, J. Meienhofer, The Peptides, Vol 3, Academic Press, New York, 1981.
[33] S.W. Bailey, R.Y. Chandrasekaran, J.E. Ayling, J. Org. Chem. 57 (1992) 4470-4474.
[34] S.V. Chankeshwara, A.K. Chakraborti, Tetrahedron Lett. 47(2006) 1087-1091.
[35] A. Heydari, R.K. Shiroodi, H. Hamadi, M. Esfandyari, M. Pourayoubi, Tetrtahedron Lett. 48 (2007) 5865-5868.
[36] S.V. Chankeshwara, A.K. Chakraborti, Synthesis 16 (2006) 2784-2788.
[37] D.J. Upadhyaya, A. Barge, R. Stefania, G. Cravotto, Tetrahedron Lett. 48 (2007) 8318-8322.
[38] B. Das, K. Venkateswarlu, M. Krishnaiah, H. Holla, Tetrahedron Lett. 47 (2006) 7551-7556.
[39] R. Varala, S. Nuvula, R. Adapa, J. Org. Chem. 71 (2006) 8283-8286.
[40] A.K. Chakraborti, S.V. Chankeshwara, Org. Biomol. Chem. 4 (2006) 2769-2771.
[41] F. Shirini, J. Albadi, Bull. Korean Chem. Soc. 31 (2010) 1119-1120.
[42] F. Shirini, M.A. Zolfigol, J. Albadi, J. Iran. Chem. Soc. 7 (2010) 895-899.
[43] F. Shirini, M.A. Zolfigol, A.R. Aliakbar, J. Albadi, Synth. Commnu. 40 (2010) 1022-1028.