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(b) Nair, V.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T.; Devi, B. R.; Menon, R. S.; Rath, N. P.; Srinivas, R. Synthesis 2003, 1895.
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For the reaction of N-tosylimines catalyzed by tertiary amines, see: (a) Li, C.-Q.; Shi, M. Org. Lett. 2003, 5, 4273.
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For the reaction of N-tosylimines catalyzed by tertiary amines, see: (a) Li, C.-Q.; Shi, M. Org. Lett. 2003, 5, 4273.
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0348041984
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(b) Zhao, G.-L.; Huang, J.-W.; Shi, M. Org. Lett. 2003, 5, 4737.
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Zhao, G.-L.1
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24
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0141885412
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For three-component coupling reaction based on Morita-Baylis-Hillman reaction, see: a
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For three-component coupling reaction based on Morita-Baylis-Hillman reaction, see: (a) Evans, C. A.; Miller, S. J. J. Am. Chem. Soc. 2003, 125, 12394.
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Miller, S.J.2
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25
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0037471214
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For nickel-catalyzed three-component coupling of alkynes and imines, see: b
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For nickel-catalyzed three-component coupling of alkynes and imines, see: (b) Patel, S.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
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Patel, S.1
Jamison, T.F.2
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26
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41149112680
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We have thoroughly explored optimal reaction conditions using various solvents, tertiary amines, time and temperature, and equivalents of the reagents. However, an improved result over a 47% yield could not be obtained. Details of these examinations are described in Supporting Information
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We have thoroughly explored optimal reaction conditions using various solvents, tertiary amines, time and temperature, and equivalents of the reagents. However, an improved result over a 47% yield could not be obtained. Details of these examinations are described in Supporting Information.
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27
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41149162413
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Besides the desired olefin products 2, unreacted imines were detected in the reaction mixture, which were hydrolyzed during a workup process.
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Besides the desired olefin products 2, unreacted imines were detected in the reaction mixture, which were hydrolyzed during a workup process.
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28
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33846250463
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For recent examples of organocatalyzed syntheses of the chromene-type skeleton from salicyl aldehydes, see: (a) Sunden, H, Ibrahem, I, Zhao, G.-L, Eriksson, L, Cordova, A. Chem, Eur. J. 2007, 13, 574
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For recent examples of organocatalyzed syntheses of the chromene-type skeleton from salicyl aldehydes, see: (a) Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Cordova, A. Chem. - Eur. J. 2007, 13, 574.
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(b) Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S.; Wang, W. Chem. Commun. 2007, 507.
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(c) Govender, T.; Hojabri, L.; Moghaddam, F. M.; Arvidsson, P. I. Tetrahedron: Asymmetry 2006, 17, 1763.
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Tetrahedron: Asymmetry
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Considering harmfulness of benzene, the reaction of 5a was investigated using toluene as an alternative solvent, providing a comparable result (110°C, 3 h, 72% yield) with the case of benzene.
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Considering harmfulness of benzene, the reaction of 5a was investigated using toluene as an alternative solvent, providing a comparable result (110°C, 3 h, 72% yield) with the case of benzene.
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35
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41149153111
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We suppose that the mechanism of the cyclization reaction (formation of 8) follows the same pathway as depicted in Scheme 2 in an intramolecular fashion because the same reaction in the presence of CD3-OD (this deuterium ought to be exchanged for the phenolic hydrogen of 5) gave the product 6 in which the deuterium was incorporated at the 2-position (as well as the methoxy hydrogens).
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We suppose that the mechanism of the cyclization reaction (formation of 8) follows the same pathway as depicted in Scheme 2 in an intramolecular fashion because the same reaction in the presence of CD3-OD (this deuterium ought to be exchanged for the phenolic hydrogen of 5) gave the product 6 in which the deuterium was incorporated at the 2-position (as well as the methoxy hydrogens).
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36
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22244463229
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For recent reports on chromene-forming reaction of salicyl N- tosylimine and conjugated alkynes or allenic esters, relating to our reaction systems but via a different reaction pathway, see: (a) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
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For recent reports on chromene-forming reaction of salicyl N- tosylimine and conjugated alkynes or allenic esters, relating to our reaction systems but via a different reaction pathway, see: (a) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
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(b) Guo, Y.-W.; Shi, Y.-L.; Li, H.-B.; Shi, M. Tetrahedron 2006, 62, 5875.
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0001258123
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For reports on allylation of benzopyrylium derivatives, see: a
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For reports on allylation of benzopyrylium derivatives, see: (a) Lee, Y. G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
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