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Synthesis of 4-Chloro-5,6-dihydro-2H-pyran Derivatives by NbCl5 Mediated Cyclization of Epoxides with Homopropargylic Alcohols
Corresponding Author(s) : K. Rajasekhar
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
Epoxides undergoes cyclization with homopropargylic alcohols in the presence of niobium pentachloride under mild condition to afford the corresponding dihydropyran derivatives in good yield.
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- T. Oishi and Y. Ohtsuka, in ed.: Atta-ur-Rahman, Studies in Natural Products Synthesis, Elsevier, Amsterdam, vol. 3, p. 73 (1989).
- L. Yet, Chem. Rev., 100, 2963 (2000).
- T.L.B. Boivin, Tetrahedron, 43, 3309 (1987).
- L. Coppi, A. Ricci and M. Taddei, J. Org. Chem., 53, 911 (1988).
- W.-C. Zhang and C.-J. Li, Tetrahedron, 56, 2403 (2000).
- B. Schmidt and M. Westhus, Tetrahedron, 56, 2421 (2000).
- A.P. Dobbs and S. Martinovic, Tetrahedron Lett., 43, 7055 (2002).
- P.O. Miranda, D.D. Diaz, J.I. Padron, J. Bermejo and V.S. Martin, Org. Lett., 5, 1979 (2003).
- C.M. Yu, M.S. Shin and E.Y. Cho, Bull. Korean Chem. Soc., 25, 1625 (2004).
- P.O. Miranda, R.M. Carballo, V.S. Martin and J.I. Padron, Org. Lett., 11, 357 (2009).
- J.S. Yadav, K. Rajasekhar and M.S.R. Murty, Tetrahedron Lett., 47, 6149 (2006).
- T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 45, 49 (2004).
- I. Mohammadpoor-Baltork and H. Aliyan, Synth. Commun., 28, 3943 (1998).
- I. Mohammadpoor-Baltork, S. Tangestaninejad, H. Aliyan and V. Mirkhani, Synth. Commun., 30, 2365 (2000).
- I. Mohammadpoor-Baltork, A.R. Khosropour and H. Aliyan, Synth. Commun., 31, 3411 (2001).
- N. Raghavendra Swamy, G. Kondaji and K. Nagaiah, Synth. Commun., 32, 2307 (2002).
- T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 43, 7891 (2002).
- K. Suzuki, T. Hashimoto, H. Maeta and T. Matsumoto, Synlett, 125 (1992).
- C.K.Z. Andrade, N.R. Azevedo and G.R. Oliveira, Synthesis, 928 (2002).
References
T. Oishi and Y. Ohtsuka, in ed.: Atta-ur-Rahman, Studies in Natural Products Synthesis, Elsevier, Amsterdam, vol. 3, p. 73 (1989).
L. Yet, Chem. Rev., 100, 2963 (2000).
T.L.B. Boivin, Tetrahedron, 43, 3309 (1987).
L. Coppi, A. Ricci and M. Taddei, J. Org. Chem., 53, 911 (1988).
W.-C. Zhang and C.-J. Li, Tetrahedron, 56, 2403 (2000).
B. Schmidt and M. Westhus, Tetrahedron, 56, 2421 (2000).
A.P. Dobbs and S. Martinovic, Tetrahedron Lett., 43, 7055 (2002).
P.O. Miranda, D.D. Diaz, J.I. Padron, J. Bermejo and V.S. Martin, Org. Lett., 5, 1979 (2003).
C.M. Yu, M.S. Shin and E.Y. Cho, Bull. Korean Chem. Soc., 25, 1625 (2004).
P.O. Miranda, R.M. Carballo, V.S. Martin and J.I. Padron, Org. Lett., 11, 357 (2009).
J.S. Yadav, K. Rajasekhar and M.S.R. Murty, Tetrahedron Lett., 47, 6149 (2006).
T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 45, 49 (2004).
I. Mohammadpoor-Baltork and H. Aliyan, Synth. Commun., 28, 3943 (1998).
I. Mohammadpoor-Baltork, S. Tangestaninejad, H. Aliyan and V. Mirkhani, Synth. Commun., 30, 2365 (2000).
I. Mohammadpoor-Baltork, A.R. Khosropour and H. Aliyan, Synth. Commun., 31, 3411 (2001).
N. Raghavendra Swamy, G. Kondaji and K. Nagaiah, Synth. Commun., 32, 2307 (2002).
T. Ollevier and G. Lavie-Compin, Tetrahedron Lett., 43, 7891 (2002).
K. Suzuki, T. Hashimoto, H. Maeta and T. Matsumoto, Synlett, 125 (1992).
C.K.Z. Andrade, N.R. Azevedo and G.R. Oliveira, Synthesis, 928 (2002).