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For a recent overview of the synthesis and application of 2-imidazolines, see
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For a recent overview of the synthesis and application of 2-imidazolines, see: N. Elders, R. F. Schmitz, F. J. J. de Kanter, E. Ruijter, M. B. Groen, R. V. A. Orru, J. Org. Chem. 2007, 72, 6135-6142.
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22
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53849144123
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1 increases the a acidity and terminal C electrophilicity of the isocyanide (also see ref. [6b]).
-
1 increases the a acidity and terminal C electrophilicity of the isocyanide (also see ref. [6b]).
-
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23
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53849108605
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For a recent overview of the synthesis and reactions of oxazoles as well as oxazole-containing natural products, see: a) D. C. Palmer, Oxazoles: Synthesis, Reactions, and Spectroscopy, part A, Wiley, New Jersey USA, 2003;
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For a recent overview of the synthesis and reactions of oxazoles as well as oxazole-containing natural products, see: a) D. C. Palmer, Oxazoles: Synthesis, Reactions, and Spectroscopy, part A, Wiley, New Jersey (USA), 2003;
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24
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40
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2042466880
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For intramolecular oxazole formation from α-acidic isocyanides, see: a
-
For intramolecular oxazole formation from α-acidic isocyanides, see: a) I. Maeda, K. Togo, R. Yoshida, Bull. Chem. Soc. Jpn. 1971, 44, 1407-1410;
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84936277265
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d) R. Schröder, U. Schöllkopf, E. Blume, I. Hoppe, Liebigs Ann. Chem. 1975, 533-546;
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17844398818
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e) J. P. Chupp, J. J. D'Amico, K. L. Leschinsky, J. Org. Chem. 1978, 43, 3553-3559;
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34249972856
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i) V. V. Mishchenko, Z. I. Itov, S. D. L'vova, G. K. Shostakovskaya, V. I. Gunar, Phar. Chem. J. 1988, 22, 568-572.
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49
-
-
53849094605
-
-
I makes the (free) electron pair less reactive towards reaction with the imine (Scheme 2, path III).
-
I makes the (free) electron pair less reactive towards reaction with the imine (Scheme 2, path III).
-
-
-
-
50
-
-
53849112783
-
-
3N) for the synthesis of 4n and 5n (Table 6, entry 5).
-
3N) for the synthesis of 4n and 5n (Table 6, entry 5).
-
-
-
-
51
-
-
85065147822
-
-
Although no direct evidence for the formation of isocyanobenzyl-amide is observed and direct transamidation is usually only very limited M. A. Kraus, Synthesis 1973, 361-362
-
Although no direct evidence for the formation of isocyanobenzyl-amide is observed and direct transamidation is usually only very limited (M. A. Kraus, Synthesis 1973, 361-362)
-
-
-
-
52
-
-
0005827055
-
-
fusion of ammonium salts with amides has been reported before (A. Galat, G. Elion, J. Am. Chem. Soc. 1943, 65, 1566-1567).
-
fusion of ammonium salts with amides has been reported before (A. Galat, G. Elion, J. Am. Chem. Soc. 1943, 65, 1566-1567).
-
-
-
-
53
-
-
23044449420
-
-
I, see: C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 3451-3453;
-
I, see: C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 3451-3453;
-
-
-
-
54
-
-
33750434876
-
-
I catalysis, see: D. Benito-Garagorri, V. Bocokić, K. Kirchner, Tetrahedron Lett. 2006, 47, 8641-8644.
-
I catalysis, see: D. Benito-Garagorri, V. Bocokić, K. Kirchner, Tetrahedron Lett. 2006, 47, 8641-8644.
-
-
-
-
55
-
-
53849131832
-
-
Previously, ketones were found to yield the corresponding 2-(hydroxyalkyl)oxazoles, see ref, 9k
-
Previously, ketones were found to yield the corresponding 2-(hydroxyalkyl)oxazoles, see ref. [9k].
-
-
-
-
56
-
-
53849121080
-
-
I catalysis, most likely because of the intrinsically lower nucleophilicity of the ester carbonyl oxygen in 1 d-j compared with the amide carbonyl oxygen in 1c.
-
I catalysis, most likely because of the intrinsically lower nucleophilicity of the ester carbonyl oxygen in 1 d-j compared with the amide carbonyl oxygen in 1c.
-
-
-
-
57
-
-
2342485673
-
-
For similar (and enantioselective) examples of 2-(hydroxyalkyl)oxazole formation, see: a
-
For similar (and enantioselective) examples of 2-(hydroxyalkyl)oxazole formation, see: a) G. Cuny, R. Gamez-Montano, J. Zhu, Tetrahedron 2004, 60, 4879-4886;
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34548082846
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b) S. Wang, M.-X. Wang, D.-X. Wang, J. Zhu, Eur. J. Org. Chem. 2007, 4076-4080;
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Wang, S.1
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Wang, D.-X.3
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34548534037
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c) S.-X. Wang, M.-X. Wang, D.-X. Wang, J. Zhu, Org. Lett. 2007, 9, 3615-3618.
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Wang, S.-X.1
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0010332571
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a) K. Matzumoto, M. Suzuki, N. Yoneda, M. Miyoshi, Synthesis 1977, 249-250;
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Matzumoto, K.1
Suzuki, M.2
Yoneda, N.3
Miyoshi, M.4
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62
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12344293588
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A. Fayol, C. Housseman, X. Sun, P. Janvier, H. Bienaymé, J. Zhu, Synlett 2005, 161-165.
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Synlett
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Fayol, A.1
Housseman, C.2
Sun, X.3
Janvier, P.4
Bienaymé, H.5
Zhu, J.6
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63
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37049049182
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Synthesized according to the method reported: F. P. Doyle, G. R. Fosker, J. H. C. Nayler, H. Smith, J. Chem. Soc. 1962, 1440-1444.
-
Synthesized according to the method reported: F. P. Doyle, G. R. Fosker, J. H. C. Nayler, H. Smith, J. Chem. Soc. 1962, 1440-1444.
-
-
-
-
64
-
-
53849087302
-
-
13C NMR spectrum for these type of compounds, also see ref. [6a].
-
13C NMR spectrum for these type of compounds, also see ref. [6a].
-
-
-
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