Mild and efficient solvent-free tetrahydropyranylation (THP) of alcohols catalyzed by reusable acidic ionic liquid [Et3N(CH2)4SO3H][OTs]
Subject Areas : Iranian Journal of CatalysisAbdol Reza Hajipour 1 , Ghobad Azizi 2
1 - Department of Pharmacology, University of Wisconsin Med. Sch., 1300 University Avenue, Madison, WI 53706-1532, USA
Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.
2 - Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.
Keywords:
Abstract :
[1] M. Bodanszky, Y.S. Klausner, M.A. Ondetti, Peptide synthesis, Wiley, 1976.
[2] J.H. van Boom, P.M.J. Burgers, G.R. Owen, C.B. Reese, R. Saffhill, J. Chem. Soc. Chem. Commun. (1971) 869-871.
[3] C. Augé, C.D. Warren, R.W. Jeanloz, M. Kiso, L. Anderson, Carbohydrate Res. 82 (1980) 85-95.
[4] R. Tschesche, Angew. Chem. 77 (1965) 184-184.
[5] P.G.M. Wuts, T.W. Greene, Greene's Protective Groups in Organic Synthesis, Wiley, 2006.
[6] M. Miyashita, A. Yoshikoshi, P.A. Grieco, J. Org. Chem. 42 (1977) 3772-3774.
[7] R.D. Johnston, C.R. Marston, P.E. Krieger, G.L. Goe, Synthesis (1988) 393-394.
[8] G.A. Olah, A. Husain, B.P. Singh, Synthesis (1985) 703-704.
[9] V. Bolitt, C. Mioskowski, D.S. Shin, J. Falck, Tetrahedron Lett. 29 (1988) 4583-4586.
[10] S. Hoyer, P. Laszlo, M. Orlović, E. Polla, Synthesis (1986) 655-657.
[11] Y. Morizawa, I. Mori, T. Hiyama, H. Nozaki, Synthesis (1981) 899-901.
[12] G.A. Olah, A. Husain, B.P. Singh, Synthesis (1983) 892-895.
[13] J. Yadav, D. Srinivas, G.S. Reddy, Synth. Commun. 28 (1998) 1399-1404.
[14] N. Deka, J.C. Sarma, Synth. Commun. 30 (2000) 4435-4441.
[15] N. Rezai, F.A. Meybodi, P. Salehi, Synth. Commun. 30 (2000) 1799-1805.
[16] S. Naik, R. Gopinath, B.K. Patel, Tetrahedron Lett. 42 (2001) 7679-7681.
[17] M.M. Heravi, F.K. Behbahani, H.A. Oskooie, R. Hekmat Shoar, Tetrahedron Lett. 46 (2005) 2543-2545.
[18] M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 42 (2001) 2851-2853.
[19] Y.G. Wang, X.X. Wu, Z.Y. Jiang, Tetrahedron Lett. 45 (2004) 2973-2976.
[20] A.T. Khan, S. Ghosh, L.H. Choudhury, Eur. J. Org. Chem. 2005 (2005) 4891-4896.
[21] S. Islam, A. Majee, A. Khan, Synth. Commun. 35 (2005) 1789-1793.
[22] T.S. Reddy, K. Ravinder, N. Suryakiran, M. Narasimhulu, K.C. Mahesh, Y. Venkateswarlu, Tetrahedron Lett. 47 (2006) 2341-2344.
[23] A.R. Hajipour, G. Azizi, A.E. Ruoho, Synlett (2009) 1974-1978.
[24] B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, S.V. Patil, Monatsh. Chem. 134 (2003) 425-428.
[25] A. Khazaei, A. Rostami, M. Mahboubifar, Catal. Commun. 8 (2007) 383-388.
[26] T. Mineno, Tetrahedron Lett. 43 (2002) 7975-7978.
[27] Y.-S. Hon, C.F. Lee, Tetrahedron Lett. 40 (1999) 2389-2392.
[28] B. Tamami, K. Parvanak Borujeny, Tetrahedron Lett. 45 (2004) 715-718.
[29] A.T. Khan, L.H. Choudhury, S. Ghosh, Tetrahedron Lett. 45 (2004) 7891-7894.
[30] G.P. Romanelli, G. Baronetti, H.J. Thomas, J.C. Autino, Tetrahedron Lett. 43 (2002) 7589-7591.
[31] S. Palaniappan, M. Sai Ram, C.A. Amarnath, Green Chem. 4 (2002) 369-371.
[32] L.C. Branco, C.A. Afonso, Tetrahedron 57 (2001) 4405-4410.
[33] B. Karimi, J. Maleki, Tetrahedron Lett. 43 (2002) 5353-5355.
[34] V.V. Namboodiri, R.S. Varma, Chem. Commun. (2002) 342-343.
[35] B. Choudary, V. Neeraja, M. Lakshmi Kantam, J. Mol. Catal. A: Chem. 175 (2001) 169-172.