-
5
-
-
28244457575
-
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For selected examples of reactions that occur without ring opening, see the following leading references: a) D. L. Comins, J. J. Sahn, Org. Lett. 2005, 7, 5227-5228;
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Comins, D.L.1
Sahn, J.J.2
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8
-
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33845319549
-
-
note
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Please see the Supporting Information for plausible mechanisms for these transformations.
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-
-
-
9
-
-
85069754511
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For reviews, please see : a) J. Becher, Synthesis 1980, 589-613;
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Becher, J.1
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12
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0000626592
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Also, see J. Becher, L. Finsen, I. Winckelmann, Tetrahedron 1981, 37, 2375-2378.
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Tetrahedron
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Becher, J.1
Finsen, L.2
Winckelmann, I.3
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13
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0033716747
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a) For applications of these compounds in the dye industry, see: A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 2000, 100, 1973-2011;
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Mishra, A.1
Behera, R.K.2
Behera, P.K.3
Mishra, B.K.4
Behera, G.B.5
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14
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-
84982339743
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-
b) For a two-step azulene synthesis featuring 5-amino-2,4-pentadienals, see: K. Hafner, K.-D. Asmus, Justus Liebigs Ann. Chem. 1964, 671, 31-40;
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Hafner, K.1
Asmus, K.-D.2
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15
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0033214301
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c) For one application in natural product synthesis, see: K. Jakubowicz, K. B. Abdeljelil, M. Herdemann, M.-T. Martin, A. Gateau-Olesker, A. A. Mourabit, C. Marazano, B. C. Das, J. Org. Chem. 1999, 64, 7381-7387.
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Jakubowicz, K.1
Abdeljelil, K.B.2
Herdemann, M.3
Martin, M.-T.4
Gateau-Olesker, A.5
Mourabit, A.A.6
Marazano, C.7
Das, B.C.8
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16
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0010653530
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For a comprehensive review of methods for indole synthesis, see: J. A. Joule, Sci. Synth. 2001, 10, 361-652.
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Joule, J.A.1
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31944441649
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and references therein
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b) D. F. Taber, W. Tian, J. Am. Chem. Soc. 2006, 128, 1058-1059, and references therein.
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Taber, D.F.1
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17144421373
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For a review, see: (Ed.: D. Astruc), Wiley-VCH, Weinheim, Please see the Supporting Information for experimental details
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For a review, see: A. Suzuki in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, pp. 53-106. Please see the Supporting Information for experimental details.
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Modern Arene Chemistry
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Suzuki, A.1
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20
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33845286491
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note
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Typical activating agents include 2,4-dinitrochlorobenzene, cyanogen halides, and sulfur trioxide. See references [1] and [4a].
-
-
-
-
21
-
-
33845341064
-
-
note
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The conversion of 9 into 10 could conceivably occur through an electrocyclic pathway or a simple ionic mechanism; either would be followed by simple alkene geometrical isomerizations.
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-
-
-
22
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27544485685
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and references therein
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Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15 051-15 053, and references therein. Although we suspect that the reactivity of products of type 7 will almost certainly be different from regular α,β-unsaturated aldehydes owing to the conjugation of the indole nitrogen, the incorporation of an electron-withdrawing N-protecting group might result in reasonable reactivity in iminium-based asymmetric organocatalysis. For a relevant example, please see reference [12].
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Huang, Y.1
Walji, A.M.2
Larsen, C.H.3
MacMillan, D.W.C.4
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23
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0242582464
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An indole-3-propenal was used in an asymmetric organocatalytic Diels-Alder reaction in a synthesis of hapalindole Q: A. C. Kinsman, M. A. Kerr, J. Am. Chem. Soc. 2003, 125, 14 120-14 125.
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0033593964
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For a few select examples, see: Neurological therapy: a) N. R. Curtis, J. J. Kulagowski, P. D. Leeson, M. P. Ridgill, F. Emms, S. B. Freedman, S. Patel, S. Patel, Bioorg. Med. Chem. Lett. 1999, 9, 585-588;
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Emms, F.5
Freedman, S.B.6
Patel, S.7
Patel, S.8
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b) G. A. Showell, F. Emms, R. Marwood, D. O'Connor, S. Patel, P. D. Leeson, Bioorg. Med. Chem. 1998, 6, 1-8;
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Leeson, P.D.6
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0141680855
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Antiviral therapy: c) T. Wang, Z. Zhang, O. B. Wallace, M. Deshpande, H. Fang, Z. Yang, L. M. Zadjura, D. L. Tweedie, S. Huang, F. Zhao, S. Ranadive, B. S. Robinson, Y.-F. Gong, K. Ricarrdi, T. P. Spicer, C. Deminie, R. Rose, H.-G. H. Wang, W. S. Blair, P.-Y. Shi, P.-f. Lin, R. J. Colonno, N. A. Meanwell, J. Med. Chem. 2003, 46, 4236-4239.
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Deshpande, M.4
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Yang, Z.6
Zadjura, L.M.7
Tweedie, D.L.8
Huang, S.9
Zhao, F.10
Ranadive, S.11
Robinson, B.S.12
Gong, Y.-F.13
Ricarrdi, K.14
Spicer, T.P.15
Deminie, C.16
Rose, R.17
Wang, H.-G.H.18
Blair, W.S.19
Shi, P.-Y.20
Lin, P.-F.21
Colonno, R.J.22
Meanwell, N.A.23
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