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Reactions of Methyl Acetylenecarboxylate with Heterocyclic Enamines: [2+2] Cycloadditions in Polar and Non-Polar Solvents
Corresponding Author(s) : Nesimi Uludag
Asian Journal of Chemistry,
Vol. 26 No. 4 (2014): Vol 26 Issue 4
Abstract
In this study, enamines of cyclic ketones reacting with methyl acetylenecarboxylate to produce intermadiate cyclobutene adducts have been isolated. Reactions of methyl acetylenecarboxylate with enamines derived from cyclobutene adducts and ring expansion products were described.
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- G.A. Berchtold and G.F. Uhlig, J. Org. Chem., 28, 1459 (1963); doi:10.1021/jo01041a004.
- A. Uzgoren-Baran, N. Tunoglu and G. Okay, Org. Prep. Proced. Int., 42, 143 (2010); doi:10.1080/00304941003680269.
- N. Tunoglu and N. Uludag, Org. Prep. Proced. Int., 29, 541 (1997); doi:10.1080/00304949709355230.
- C.F. Huebner, L. Dorfman, M.M. Robison, E. Donoghue, W.G. Pierson and P. Strachan, J. Org. Chem., 28, 3134 (1963); doi:10.1021/jo01046a047.
- E. Rossi, G. Abbiati, A. Arcadi and F. Marinelli, Tetrahedron Lett., 42, 3705 (2001); doi:10.1016/S0040-4039(01)00553-6.
- A.G. Cook, Enamines Structure and Reactions, M. Dekker, New York; Ch. 7 pp. 1-384 (1988).
- G. Kaupp, V. Pogodda, A. Alfah, H. Mier and A. Vierengel, Angew. Chem. Int. Ed.., 31, 767 (1992); doi:10.1002/anie.199207681.
- H. Hongo, H. Nakano and Y. Okuyama, Heterocycles, 40, 831 (1995); doi:10.3987/COM-94-S76.
- G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz and R. Terrell, J. Am. Chem. Soc., 85, 207 (1963); doi:10.1021/ja00885a021.
- G. Van Beek, J.L. Van Der Baan, G.W. Klumpp and F. Bickelhaupt, Tetrahedron, 42, 5111 (1986); doi:10.1016/S0040-4020(01)88064-9.
- G. Stork and T.L. Macdonald, J. Am. Chem. Soc., 97, 1264 (1975); doi:10.1021/ja00838a062.
- A.K. Bose and G.L. Minah, Metropolitan Regional Meeting of the American Chemical Society, Newark, New York: January 28 (1963).
- D.N. Reinhoudt, W. Verboom, G.W. Visser, W.P. Trompenaars, S. Harkema and G.J. Van Hummel, J. Am. Chem. Soc., 106, 1341 (1984); doi:10.1021/ja00317a029.
References
G.A. Berchtold and G.F. Uhlig, J. Org. Chem., 28, 1459 (1963); doi:10.1021/jo01041a004.
A. Uzgoren-Baran, N. Tunoglu and G. Okay, Org. Prep. Proced. Int., 42, 143 (2010); doi:10.1080/00304941003680269.
N. Tunoglu and N. Uludag, Org. Prep. Proced. Int., 29, 541 (1997); doi:10.1080/00304949709355230.
C.F. Huebner, L. Dorfman, M.M. Robison, E. Donoghue, W.G. Pierson and P. Strachan, J. Org. Chem., 28, 3134 (1963); doi:10.1021/jo01046a047.
E. Rossi, G. Abbiati, A. Arcadi and F. Marinelli, Tetrahedron Lett., 42, 3705 (2001); doi:10.1016/S0040-4039(01)00553-6.
A.G. Cook, Enamines Structure and Reactions, M. Dekker, New York; Ch. 7 pp. 1-384 (1988).
G. Kaupp, V. Pogodda, A. Alfah, H. Mier and A. Vierengel, Angew. Chem. Int. Ed.., 31, 767 (1992); doi:10.1002/anie.199207681.
H. Hongo, H. Nakano and Y. Okuyama, Heterocycles, 40, 831 (1995); doi:10.3987/COM-94-S76.
G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz and R. Terrell, J. Am. Chem. Soc., 85, 207 (1963); doi:10.1021/ja00885a021.
G. Van Beek, J.L. Van Der Baan, G.W. Klumpp and F. Bickelhaupt, Tetrahedron, 42, 5111 (1986); doi:10.1016/S0040-4020(01)88064-9.
G. Stork and T.L. Macdonald, J. Am. Chem. Soc., 97, 1264 (1975); doi:10.1021/ja00838a062.
A.K. Bose and G.L. Minah, Metropolitan Regional Meeting of the American Chemical Society, Newark, New York: January 28 (1963).
D.N. Reinhoudt, W. Verboom, G.W. Visser, W.P. Trompenaars, S. Harkema and G.J. Van Hummel, J. Am. Chem. Soc., 106, 1341 (1984); doi:10.1021/ja00317a029.