Abstract
Without using any catalysts, a variety of epoxides undergo ring-opening by aromatic amines to afford the corresponding 1,2-amino alcohols in high to excellent yields with good regioselectivity in the presence of water as solvent and under solvent-free conditions.
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Notes
It is difficult to distinguish in/on water in this reaction.
References
N.E. Leadbeater, Chem. Commun. 2881 (2005)
C.B. Rao, B. Chinnababu, Y. Venkateswarlu, J. Org. Chem. 74, 8856 (2009)
H.R. Hobbs, N.R. Thomas, Chem. Rev. 107, 2786 (2007)
S. Kobayashi, Y. Mori, S. Nagayama, K. Manabe, Green Chem. 1, 175 (1999)
Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. Int. Ed. 45, 958 (2006)
C-J. Li Chem. Rev.105 3095 (2005)
F. Orsini, G. Sello, T. Fumagalli, Synlett 1717 (2006)
R.V. Hangarge, S.A. Sonwane, D.V. Jarikote, M.S. Shingare, Green Chem. 3, 310 (2001)
H-B. Zhang, L. Liu, Y-J. Chen, D. Wang, C-J. Li, Eur. J. Org. Chem. 869 (2006)
F. Matloubi Moghaddam, L. Hojabri, S. Taheri, P. Pirani, J. Iran. Chem. Soc. 7, 781 (2010)
A. Hasaninejad, M. Shekouhy, A. Zare, S.M.S. Hoseini Ghattali, N. Golzar, J. Iran. Chem. Soc. 8, 411 (2011)
H. Sharghi, R. Khalifeh, F. Moeini, M.H. Beyzavi, A. Salimi Beni, M.M. Doroodmand, J. Iran. Chem. Soc. 8, S89 (2011)
K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)
S.-J. Jeon, H. Li, P.J. Walsh, J. Am. Chem. Soc. 127, 16416 (2005)
M.M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M.S. Abaee, Org. Lett. 9, 2791 (2007)
N. Azizi, F. Aryanasab, M.R. Saidi, Org. Lett. 8, 5275 (2006)
U.K. Roy, S. Roy, Tetrahedron 62, 678 (2006)
T. Hirashita, K. Mitsui, Y. Hayashi, S. Araki, Tetrahedron Lett. 45, 9189 (2004)
M.L. Kantam, S. Laha, J. Yadav, B. Sreedhar, Tetrahedron Lett. 47, 6213 (2006)
N. Iranpoor, H. Firouzabadi, M. Shekarize, Org. Biomol. Chem. 1, 724 (2003)
J. Cossy, V. Bellosta, C. Hamoir, J.-R. Desmurs, Tetrahedron Lett. 43, 7083 (2002)
T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 43, 7891 (2002)
G. Sabitha, G.S.K.K. Reddy, K.B. Reddy, J.S. Yadav, Synthesis 2298 (2003)
T. Ollevier, E. Nadeau, Tetrahedron Lett. 49, 1546 (2008)
G. Sabitha, R.S. Babu, M. Rajkumar, J.S. Yadav, Org. Lett. 4, 343 (2002)
T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 45, 49 (2004)
J.S. Yadav, B.V.S. Reddy, K. Harikishan, C. Madan, A. V. Narsaiah, Synthesis 2897 (2005)
M. Movassaghi, E.N. Jacobsen, J. Am. Chem. Soc. 124, 2456 (2002)
V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron 59, 8213 (2003)
D. Bradley, G. Williams, M. Lawton, Org. Biomol. Chem. 3, 3269 (2005)
Y. Nishiyama, C. Katahira, N. Sonoda, Tetrahedron Lett. 45, 8539 (2004)
A.D. Innocenti, A. Capperucci, A. Cerreti, S. Pollicino, S. Scapecchi, I. Malesci, G. Castagnolia, Synlett 3063 (2005)
P-Q. Zhao, L-W. Xu, C-G. Xia, Synlett 846 (2004)
P.B. Shivani, A.K. Chakraborti, J. Org. Chem. 72, 3713 (2007)
D.R. Gehlert, D.J. Goldstein, P.A. Hipskind, Ann. Rep. Med. Chem. 201 (1999)
E.J. Corey, F. Zhang, Angew. Chem. Int. Ed. 38, 1931 (1999)
C.W. Johannes, M.S. Visser, G.S. Weatherhead, A.H. Hoveyda, J. Am. Chem. Soc. 120, 8340 (1998)
B.L. Chng, A. Ganesan, Bioorg. Med. Chem. Lett. 7, 1511 (1997)
G.A. Rogers, S.M. Parsons, D.C. Anderson, L.M. Nilsson, B.A. Bahr, W.D. Kornreich, R. Kaufman, R.S. Jacobs, B. Kirtman, J. Med. Chem. 32, 1217 (1989)
J. De Cree, H. Geukens, J. Leempoels, H. Verhaegen, Drug Dev. Res. 8, 109 (1986)
Y. Harrak, M.D. Pujol, Tetrahedron Lett. 43, 819 (2002)
N. Azizi, M.R. Saidi, Tetrahedron 63, 888 (2007)
R.I. Kureshy, S. Singh, N.H. Khan, S.H.R. Abdi, S. Agrawal, V.J. Mayani, R.V. Jasra, Tetrahedron Lett. 47, 5277 (2006)
R.I. Kureshy, S. Singh, N.H. Khan, S.H.R. Abdi, S. Agrawal, V.J. Mayani, R.V. Jasra, Tetrahedron Lett. 47, 5277 (2006)
S. Rampalli, S.S. Chaudhari, K.G. Akamanchi, Synthesis 78 (2000)
F. Carree, R. Gil, J Collin Tetrahedron Lett. 45, 7749 (2004)
A. Kamal, R. Ramu, M.A. Azhar, R.G.B. Khanna, Tetrahedron Lett. 46, 2675 (2005)
I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolinc, V. Vinkovic, Tetrahedron 59, 2435 (2003)
S. Bonollo, F. Fringuelli, F. Pizzo, L. Vaccaro, Green Chem. 8, 960 (2006)
N. Azizi, M.R. Saidi, Org. Lett. 7, 3649 (2005)
A. Ziyaei-Halimehjani, K. Marjani, A. Ashouri, Green Chem. 12, 1306 (2010)
F. Rajabi, S. Ghiasian, M.R. Saidi, Green Chem. 12, 1349 (2010)
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei-Halimehjani, M.R. Saidi, J. Org. Chem. 71, 3634 (2006)
A. Ziyaei-Halimehjani, F. Aryanasab, M.R. Saidi, Tetrahedron Lett. 50, 1441 (2009)
A. Ziyaei-Halimehjani, M.R. Saidi, Tetrahedron Lett. 49, 1244 (2008)
N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8, 2079 (2006)
H. Danafar, B. Yadollahi, Catal. Commun. 10, 842 (2009)
Acknowledgments
We are grateful to the research council of Sharif University of Technology for financial support. We also thank the Faculty of Chemistry of Tarbiat Moallem University for supporting this work.
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Ziyaei-Halimehjani, A., Gholami, H. & Saidi, M.R. Catalyst-free regioselective ring opening of epoxides with aromatic amines in water and solvent-free conditions. J IRAN CHEM SOC 10, 7–11 (2013). https://doi.org/10.1007/s13738-012-0122-3
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DOI: https://doi.org/10.1007/s13738-012-0122-3