Abstract
A simple and efficient method has been developed for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines in the presence of CuFe2O4 nanoparticles as a heterogeneous recyclable catalyst at room temperature in high yields.
Similar content being viewed by others
References
B.M. Teresa, J.C.M. Adilia, C.D. Maycockd, T. Michaud, Tetrahedron 61, 7960–7966 (2005)
E.J. Corey, F. Zhang, Angew. Chem. Int. Ed. Engl. 38, 1931–1934 (1999)
C.W. Johannes, M.S. Visser, G.S. Weatherhead, A.H. Hoveyda, J. Am. Chem. 120, 8340–8347 (1998)
P. O’Brien, Angew. Chem. Int. Ed. Engl. 38, 326–329 (1999)
G. Li, H.T. Chang, K.B. Sharpless, Angew. Chem. Int. Ed. Engl. 35, 451–454 (1996)
D.J. Ager, I. Prakash, S.R. Schaad, Chem. Rev. 96, 835–876 (1996)
G. Huerta, G.C. Ordonez, C. Alvarez-Toledano, V. Santes, E. Gomez, R.A. Toscano, Synth. Commun. 34, 2393–2406 (2004)
S.W. Wei, K.A. Stingl, K.M. Weiss, S.B. Tsogoeva, Synlett 5, 707–711 (2010)
D.M. Hodgson, A.R. Gibbs, G.P. Lee, Tetrahedron 52, 14361–14384 (1996)
R.M. Hanson, Chem. Rev. 91, 437–475 (1991)
A.S. Rao, S.K. Paknikar, J.G. Kirtane, Tetrahedron 39, 2323–2367 (1983)
J.A. Deyrup, C.L. Moyer, J. Org. Chem. 34, 175–179 (1969)
P.A. Crooks, R. Szyudler, Chem. Ind., 1111–1112 (1973)
H. Eshghi, M. Rahimizadeh, A. Shoryabi, J. Iran. Chem. Soc. 2, 155–160 (2005)
M. Hosseini-Sarvari, H. Sharghi, J. Iran. Chem. Soc. 5, 384–393 (2008)
D.B.G. Williams, M. Lawton, Tetrahedron Lett. 47, 6557–6560 (2006)
A. Procopio, M. Gaspari, M. Nardi, M. Oliverio, O. Rosati, Tetrahedron Lett. 49, 2289–2293 (2008)
L.R. Reddy, M.A. Reddy, N. Bhanumathi, K.R. Rao, New J. Chem. 25, 221–222 (2001)
T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 43, 7891–7893 (2002)
M.C. Singh, R.K. Peddinti, Tetrahedron Lett. 48, 7354–7357 (2007)
A.K. Chakraborti, A. Kondaskar, Tetrahedron Lett. 44, 8315–8319 (2003)
J.R. Rodriguez, A. Navarro, Tetrahedron Lett. 45, 7495–7498 (2004)
G. Sundararajan, K. Vijayakrishna, B. Varghese, Tetrahedron Lett. 45, 8253–8256 (2004)
A. Kamal, R.R. Ramu, M.A. Azhar, G.B.R. Khanna, Tetrahedron Lett. 46, 2675–2677 (2005)
M. Maheswara, K.S.V.K. Rao, J.Y. Do, Tetrahedron Lett. 49, 1795–1800 (2008)
J.S. Yadav, B.V.S. Reddy, A.K. Basak, A.V. Narasaiah, Tetrahedron Lett. 44, 1047–1050 (2003)
H. Kotsuki, T. Shimanouchi, M. Teraguchi, M. Kataoka, A. Tatsukawa, H. Nishizawa, Chem. Lett., 2159–2162 (1994)
A.K. Chakraborti, S. Rudrawar, A. Kondaskar, Org. Biomol. Chem. 2, 1277–1280 (2004)
B.M. Reddy, K.M. Patil, B.T. Reddy, S.E. Park, Catal. Commun. 9, 950–954 (2008)
M.J. Bhanushali, N.S. Nandurkar, M.D. Bhor, B.M. Bhanage, Tetrahedron Lett. 49, 3672–3676 (2008)
S. Chikazumi, S. Taketomi, M. Ukita, M. Mizukami, H. Miyajima, M. Setogawa, Y. Kurihara, J. Magn. Magn. Mater. 65, 245–251 (1987)
A.H. Lu, W. Schmidt, N. Matoussevitch, H. Pnnermann, B. Spliethoff, B. Tesche, E. Bill, W. Kiefer, F. Schüth, Angew. Chem. 116, 4403–4410 (2004)
S.C. Tsang, V. Caps, I. Paraskevas, D. Chadwick, D. Thompsett, Angew. Chem. 116, 5763–5767 (2004)
T. Hyeon, Chem. Commun., 927–934 (2003)
D.W. Elliott, W.X. Zhang, Environ. Sci. Technol. 35, 4922–4926 (2001)
M. Takafuji, S. Ide, H. Ihara, Z. Xu, Chem. Mater. 16, 1977–1983 (2004)
I. Nedkov, R.E. Vandenberghe, T. Marinova, Ph. Thailhades, T. Merodiiska, I. Avramova, Magnetic CuFe2O4 nanoparticles were prepared according to literature. Appl. Surf. Sci. 253, 2589–2596 (2006)
I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolinčić, V. Vinković, Tetrahedron 59, 2435–2439 (2003)
H. Danafar, B. Yadollahi, Catal. Commun. 10, 842–847 (2009)
A.T. Placzek, J.L. Donelson, R. Trivedi, R.A. Gibbs, S.K. De, Tetrahedron Lett. 46, 9029–9034 (2005)
N. Azizi, M.R. Saidi, Org. Lett. 7, 3649–3651 (2005)
M.M. Mojtahedi, M.S. Abaee, V. Hamidi, Catal. Commun. 8, 1671–1674 (2007)
A.T. Placzek, J.L. Donelson, R. Trivedi, A.R. Gibbs, S.K. De, Tetrahedron Lett. 46, 9029–9034 (2005)
Acknowledgments
We would like to thank the Islamic Azad University; Ayatollah Amoli Branch for generous financial support of the research project.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Baghbanian, S.M., Farhang, M. Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines catalyzed by CuFe2O4 nanoparticles. J IRAN CHEM SOC 10, 1033–1037 (2013). https://doi.org/10.1007/s13738-013-0241-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-013-0241-5