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for cross-coupling reactions between metalated piperidines and organic halides, see: e
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for cross-coupling reactions between metalated piperidines and organic halides, see: e) J. S. Kiely, E. Laborde, L. E. Lesheski, R. A. Bucsh, J. Heterocycl. Chem. 1991, 28, 1581-1585;
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33947466070
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For other synthetic routes to 1, see: a C. J. Schmidle, R. C. Mansfield, J. Am. Chem. Soc. 1956, 78, 425-428;
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For other synthetic routes to 1, see: a) C. J. Schmidle, R. C. Mansfield, J. Am. Chem. Soc. 1956, 78, 425-428;
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21
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0000068950
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24
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36749039141
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For iodide-promoted allenyl acyliminium ion cyclization reactions, see: a
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For iodide-promoted allenyl acyliminium ion cyclization reactions, see: a) W. G. Beyersbergen van Henegouwen, R. M. Fieseler, F. P. J. T. Rutjes, H. Hiemstra, Angew. Chem. 1999, 111, 2351- 2355;
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Beyersbergen van Henegouwen, W.G.1
Fieseler, R.M.2
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Hiemstra, H.4
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0000825815
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Angew. Chem. Int. Ed. 1999, 38, 2214-2217;
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26
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b) W. G. Beyersbergen van Henegouwen, R. M. Fieseler, F. P. J. T. Rutjes, H. Hiemstra, J. Org. Chem. 2000, 65, 8317-8325.
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Beyersbergen van Henegouwen, W.G.1
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Rutjes, F.P.J.T.3
Hiemstra, H.4
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27
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0042745386
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For reviews on the multicomponent synthesis of heterocycles, see: a
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For reviews on the multicomponent synthesis of heterocycles, see: a) R. V. A. Orru, M. de Greef, Synthesis 2003, 1471-1499;
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Orru, R.V.A.1
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Tsukamoto, H.1
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b) H. Tsukamoto, T. Ueno, Y. Kondo, Org. Lett. 2007, 9, 3033-3036;
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Tsukamoto, H.1
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c) H. Tsukamoto, T. Matsumoto, Y. Kondo, J. Am. Chem. Soc. 2008, 130, 388-389.
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Tsukamoto, H.1
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33
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0000837947
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0-catalyzed tetrahydropyridine syntheses based on the carbocyclization of a 3,4-pentadienylamine with an organic halide to form both a carbon-carbon bond at C5 and a C6-N1 bond. The products of the latter reactions are often contaminated by the corresponding 2-alkenyl azetidine and 2,3-dihydropyrrole as by-products: a F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens, H. E. Schoemaker, Org. Lett. 1999, 1, 717-720;
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0-catalyzed tetrahydropyridine syntheses based on the carbocyclization of a 3,4-pentadienylamine with an organic halide to form both a carbon-carbon bond at C5 and a C6-N1 bond. The products of the latter reactions are often contaminated by the corresponding 2-alkenyl azetidine and 2,3-dihydropyrrole as by-products: a) F. P. J. T. Rutjes, K. C. M. F. Tjen, L. B. Wolf, W. F. J. Karstens, H. E. Schoemaker, Org. Lett. 1999, 1, 717-720;
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Ohno, H.1
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d) S. Ma, F. Yu, J. Li, W. Gao, Chem. Eur. J. 2007, 13, 247-254.
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Ma, S.1
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37
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53549083113
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Awide variety of starting materials 9 and 10 can be prepared by two-component coupling reactions, that is, the nucleophilic substitution of the methanesulfonate of a 3-butyn-1-ol or 2,3-butadien-1-ol with a primary amine, or the reductive amination of an aldehyde with a primary 3-butynylamine or 2,3-butadienylamine.
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Awide variety of starting materials 9 and 10 can be prepared by two-component coupling reactions, that is, the nucleophilic substitution of the methanesulfonate of a 3-butyn-1-ol or 2,3-butadien-1-ol with a primary amine, or the reductive amination of an aldehyde with a primary 3-butynylamine or 2,3-butadienylamine.
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38
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53549092921
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Paraformaldehyde is not suitable as a source of formaldinium ion
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Paraformaldehyde is not suitable as a source of formaldinium ion.
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39
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53549112644
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We observed that the use of aryl boronic esters also leads to an increase in product yields; thus, the acid moiety of electron-deficient aryl boronic acids appears to hamper the reaction
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We observed that the use of aryl boronic esters also leads to an increase in product yields; thus, the acid moiety of electron-deficient aryl boronic acids appears to hamper the reaction.
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40
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53549131414
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[7] neither alkynyl amines with internal alkyne groups nor 4-pentynylamines undergo cyclization.
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[7] neither alkynyl amines with internal alkyne groups nor 4-pentynylamines undergo cyclization.
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