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For reviews, see: a) E. R. Jarvo, S. J. Miller, Tetrahedron, 2002, 58, 2481;
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b) M. A. Convery, A. P. Davis, C. J. Dunne, J. W. MacKinnon, Tetrahedron Lett. 1995, 36, 4279;
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c) J. Dijkink, K. Eriksen, K. Goubitz, M. N. A. Van Zanden, H. Hiemstra, Tetrahedron: Asymmetry 1996, 7, 515;
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20
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0141741413
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For recent selected examples of nucleophilic reactions of azides, see: a) P. G. Reddy, B. Vahghese S. Baskaran, Org. Lett. 2003, 5, 583;
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24
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0037120838
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and references therein
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For recent selected examples of 1,3-dipolar cycloadditions of azides, see: a) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12 210, and references therein;
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0038541849
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and references therein
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b) S. Kamijo, T. Jin, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 7786, and references therein;
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26
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0038788894
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and references therein
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c) N. Shangguan, S. Katukojvala, R. Greenberg, L. J. Williams, J. Am. Chem. Soc. 2003, 125, 7754, and references therein;
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27
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0000777334
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d) for a related reaction of azides bearing an electron-withdrawing functional group and a highly strained enamine to afford amidines, see: J. K. Crandall, L. C. Crawley, J. B. Komin, J. Org. Chem. 1975, 40, 2045.
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29
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For an application to total synthesis, see: b) F. He, B. M. Foxman, B. B. Snider, J. Am. Chem. Soc. 1998, 120, 6417.
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He, F.1
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30
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0842342422
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For examples of aza-Wittig cyclizations at an amide carbonyl, usually suffering from low yields, see: a) Y. G. Gololobov, N. I. Gusar, M. P. Chaus, Tetrahedron, 1985, 41, 1823;
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0007999642
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b) P. Molina, M. Alajarín, C. López-Leonardo, I. Madrid, C. Foces-Foces, F. H. Cano, Tetrahedron 1989, 45, 1823;
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32
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0026555121
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c) J. Kurita, T. Iwata, S. Yasuike, T. Tsuchiya, J. Chem. Soc. Chem. Commun. 1992, 81;
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Kurita, J.1
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24544438352
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d) M. Alajarín, P. Molina, Á. Vidal, F. Tovar, Synlett 1988, 1288.
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Alajarín, M.1
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Vidal, Á.3
Tovar, F.4
-
34
-
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0842342425
-
-
note
-
Confirmed by TLC and LC-MS analysis.
-
-
-
-
35
-
-
0842342428
-
-
note
-
In the thiolactam method, as illustrated in Scheme 1, at least four steps are required including nonproductive protection-depro-tection reactions because of the high reactivity of the amino functionality (see refs. [3a], [3b], and [6c] for details).
-
-
-
-
36
-
-
84984199867
-
-
W. Müller, W. Dorsch, F. Effenberger, Chem. Ber. 1987, 120, 55.
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Chem. Ber.
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Müller, W.1
Dorsch, W.2
Effenberger, F.3
-
37
-
-
0842342418
-
-
note
-
For the preparation of starting material, see the Supporting Information.
-
-
-
-
38
-
-
0842299386
-
-
note
-
13C NMR spectroscopy. Therefore, the cyclization step would be faster when oxalyl bromide is used.
-
-
-
-
39
-
-
0842277629
-
-
note
-
Synthetic procedure reported by Kotsuki et al. (in ref. [3a]) was as follows; 1. hydrogenation of the azide, 2. Boc protection of the resulting amine, 3. thioamide formation with Lawesson's reagent, 4. activation of thioamide (MeI) followed by Boc deprotection and cyclization (trifluoroacetic acid).
-
-
-
-
40
-
-
0003114395
-
-
For reviews, see: a) G. Köbrich, Angew. Chem. 1973, 85, 494; Angew. Chem. Int. Ed. Engl. 1973, 12, 464;
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(1973)
Angew. Chem.
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, pp. 494
-
-
Köbrich, G.1
-
41
-
-
84982383976
-
-
For reviews, see: a) G. Köbrich, Angew. Chem. 1973, 85, 494; Angew. Chem. Int. Ed. Engl. 1973, 12, 464;
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(1973)
Angew. Chem. Int. Ed. Engl.
, vol.12
, pp. 464
-
-
-
43
-
-
0842277632
-
-
note
-
In situ IR spectra were recorded on a ReactIR 4000 instrument from ASI Applied Systems.
-
-
-
-
44
-
-
0010785608
-
-
The value was in good agreement with that from a similar compound: B. A. Phillips, G. Fodor, J. Gal, F. Letourneau, J. J. Ryan, Tetrahedron 1973, 29, 3309.
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(1973)
Tetrahedron
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, pp. 3309
-
-
Phillips, B.A.1
Fodor, G.2
Gal, J.3
Letourneau, F.4
Ryan, J.J.5
-
45
-
-
0842277630
-
-
note
-
-1 as a characteristic absorption. See the Supporting Information.
-
-
-
-
46
-
-
0842320830
-
-
note
-
++H]) derived from 2·HBr.
-
-
-
-
47
-
-
0842320828
-
-
note
-
Oxalyl bromide alone did not brominate anisole.
-
-
-
|