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6
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0027491837
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For examples of the synthesis of substituted indoles from gramine fragmentations, see: (a) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1993, 115, 9323.
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(b) Smith, A. B., III; Haseltine, J. N.; Visnick, M. Tetrahedron 1989, 45, 2431.
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Smith A.B. III1
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8
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0009649895
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Houlihan, W. J., Ed.; Heterocyclic Compounds; Wiley-Interscience: New York
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(c) Remers, W. A.; Brown, R. K. In Indoles; Houlihan, W. J., Ed.; Heterocyclic Compounds; Wiley-Interscience: New York, 1972; Part One, pp 200-203.
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Remers, W.A.1
Brown, R.K.2
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9
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0000702878
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Radical reactions are generally run under neutral conditions. See: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
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Jasperse, C.P.1
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0034614732
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(b) Bowman, W. R.; Bridge, C. F.; Brookes, P. J. Chem. Soc., Perkin Trans. 1 2000, 1.
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Bowman, W.R.1
Bridge, C.F.2
Brookes, P.3
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11
-
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0342473241
-
-
For examples of the generation of indolenines in the presence of sensitive functionality, see ref 4
-
For examples of the generation of indolenines in the presence of sensitive functionality, see ref 4.
-
-
-
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12
-
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0001146788
-
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For a review of cascade sequences in organic synthesis, see: Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195.
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Parsons, P.J.1
Penkett, C.S.2
Shell, A.J.3
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13
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0033609901
-
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For a preliminary account of this work see: Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
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Tetrahedron Lett.
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Rainier, J.D.1
Kennedy, A.R.2
Chase, E.3
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14
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0000979450
-
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Curran and co-workers have developed and applied isonitrile-alkyne radical cyclizations in synthesis. See: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127.
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J. Am. Chem. Soc.
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Curran, D.P.1
Liu, H.2
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15
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33751141093
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(b) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683.
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Curran, D.P.1
Ko, S.-B.2
Josien, H.3
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16
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0031934061
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(c) Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem. Eur. J. 1998, 4, 67.
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Josien, H.1
Ko, S.-B.2
Bom, D.3
Curran, D.P.4
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17
-
-
0029083476
-
-
Nanni and co-workers have also investigated arylisonitrile-alkyne radical reactions. See: Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045.
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Nanni, D.1
Pareschi, P.2
Rizzoli, C.3
Sgarabotto, P.4
Tundo, A.5
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18
-
-
0001451085
-
-
For other isonitrile radical reactions, see: (a) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 6, 177.
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Chem. Rev.
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Ryu, I.1
Sonoda, N.2
Curran, D.P.3
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20
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0343342687
-
-
References 9, 10, 12, 13, and 27
-
(c) References 9, 10, 12, 13, and 27.
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21
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0000352286
-
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Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127.
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J. Am. Chem. Soc.
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Fukuyama, T.1
Chen, X.2
Peng, G.3
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22
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-
0000041025
-
-
Aryl isonitrile-alkene cyclizations have been used to generate complex indoles. See ref 12 and: (a) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043.
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J. Heterocycl. Chem.
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Kobayashi, Y.1
Fukuyama, T.2
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23
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0033582790
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(b) Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519.
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Tetrahedron Lett.
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Kobayashi, S.1
Peng, G.2
Fukuyama, T.3
-
24
-
-
0034607923
-
-
A possible complication with the mechanism depicted in Scheme 1 is the intermolecular addition of the radical to the alkyne rather than the isonitrile. See: Leardini, R.; Nanni, D.; Zanardi, G. J. Org. Chem. 2000, 65, 2763.
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J. Org. Chem.
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Leardini, R.1
Nanni, D.2
Zanardi, G.3
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25
-
-
0000402423
-
-
Ito and co-workers have demonstrated that the anionic cyclization of arylisonitriles having pendant alkynes provides quinolines. See: Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
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Suginome, M.1
Fukuda, T.2
Ito, Y.3
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27
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85005647840
-
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Obrecht, R.; Hermann, R.; Ugi, I. Synthesis 1985, 4, 400.
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Synthesis
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Obrecht, R.1
Hermann, R.2
Ugi, I.3
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28
-
-
0343778342
-
-
-1)
-
-1).
-
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29
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0027214632
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Ishibashi, H.; Nishida, K.; Ikeda, M. Synth. Commun. 1993, 23, 2381.
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Synth. Commun.
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Ishibashi, H.1
Nishida, K.2
Ikeda, M.3
-
30
-
-
0342907593
-
-
The protodestannylated products were more robust and thus easier to purify than the 2-stannylindoles
-
The protodestannylated products were more robust and thus easier to purify than the 2-stannylindoles.
-
-
-
-
31
-
-
1942460739
-
-
Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M. Tetrahedron 1982, 38, 3347.
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Tetrahedron
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Tamao, K.1
Kodama, S.2
Nakajima, I.3
Kumada, M.4
-
33
-
-
77954853973
-
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For examples of silicon's influence on free-radical cyclizations, see: (a) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
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Synlett
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Gillmann, T.1
Hülsen, T.2
Massa, W.3
Wocadlo, S.4
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34
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0033525049
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(b) Shi, C.; Zhang, Q.; Wang, K. K. J. Org. Chem. 1999, 64, 925.
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Shi, C.1
Zhang, Q.2
Wang, K.K.3
-
36
-
-
0342473240
-
-
10d was isolated as the 2-tributylstannylquinoline adduct. Acidic workup failed to give protodestannylated product
-
10d was isolated as the 2-tributylstannylquinoline adduct. Acidic workup failed to give protodestannylated product.
-
-
-
-
37
-
-
0342907592
-
-
We have attempted to couple the intermediate indolenine with diethylamine, aniline, benzylamine, and methanol
-
We have attempted to couple the intermediate indolenine with diethylamine, aniline, benzylamine, and methanol.
-
-
-
-
38
-
-
0030042667
-
-
3SnH in hydride reductions of imminium ions, see: Palmisano, G.; Lesma, G.; Nali, M.; Rindone, B.; Tollari, S. Synthesis 1985, 1072.
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Enholm, E.J.1
Whitley, P.E.2
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39
-
-
0001862747
-
-
3SnH in hydride reductions of imminium ions, see: Palmisano, G.; Lesma, G.; Nali, M.; Rindone, B.; Tollari, S. Synthesis 1985, 1072.
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(1985)
Synthesis
, pp. 1072
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-
Palmisano, G.1
Lesma, G.2
Nali, M.3
Rindone, B.4
Tollari, S.5
-
40
-
-
0001226141
-
-
(a) Saegusa first demonstrated the reactivity of isonitriles with thiol radicals. See: Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118.
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Saegusa, T.1
Kobayashi, S.2
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41
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0000874522
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More recently, Bachi and Nanni have independently coupled thiol radicals with isonitriles. See: (b) Bachi, M. D.; Balanov, A.; Bar-Ner, N. J. Org. Chem. 1994, 59, 7752.
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0032554907
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(c) Camaggi, C. M.; Leardini, R.; Nanni, D.; Zanardi, G. Tetrahedron 1998, 54, 5587.
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Camaggi, C.M.1
Leardini, R.2
Nanni, D.3
Zanardi, G.4
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43
-
-
0342473239
-
-
It is not clear to us at the present time whether thiol addition to 4a (R = thioether, R′ = TMS) is occurring heterolytically or homolytically. Both would lead to bis-thiol indoles
-
It is not clear to us at the present time whether thiol addition to 4a (R = thioether, R′ = TMS) is occurring heterolytically or homolytically. Both would lead to bis-thiol indoles.
-
-
-
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46
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0001166977
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For a review on the reductive metalation of phenyl thioethers see: Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152.
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Cohen, T.1
Bhupathy, M.2
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0027999898
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For an example of the reductive metalation of thiomethylsilanes see: Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731.
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Corey, E.J.1
Chen, Z.2
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48
-
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0001288257
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For an example of the fluoride-induced heterolytic fragmentation of benzylic TMS compounds to the corresponding anions see: Ricci, A.; Fiorenza, M.; Grifagni, M. A.; Bartolini, G. Tetrahedron Lett. 1982, 23, 5079.
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Ricci, A.1
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0000052926
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Somei, M.; Karasawa, Y.; Kaneko, C. Heterocycles 1981, 16, 941.
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0017308082
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Stork, G.; Leong, A. Y. W.; Touzin, A. M. J. Org. Chem. 1976, 41, 3491.
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Touzin, A.M.3
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53
-
-
0343778340
-
-
We believe that bis-thioindole 32 comes from an irreversible coupling reaction between ethanethiol and phosphonium salt 35 (Scheme 2)
-
We believe that bis-thioindole 32 comes from an irreversible coupling reaction between ethanethiol and phosphonium salt 35 (Scheme 2).
-
-
-
-
55
-
-
0030037137
-
-
Isolation: (a) Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527.
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Osada, H.5
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56
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0031060189
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Synthesis
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(b) Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1997, 53, 59. Synthesis:
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Cui, C.-B.1
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57
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0032482105
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(a) Edmondson, S. D.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1138.
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Edmondson, S.D.1
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58
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0003526242
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Org 843
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(b) Overman, L. E.; Rosen, M. D.; Osada, H.; Shaka, A. J.; Taylor, N. D. 219th ACS National Meeting, 2000, Org 843.
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219th ACS National Meeting
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Overman, L.E.1
Rosen, M.D.2
Osada, H.3
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Taylor, N.D.5
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59
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77956820342
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Other natural products containing spiro-fused indoles include the aspidospermine alkaloids. For example, see: Saxton, J. E. Nat. Prod. Rep. 1987, 4, 591.
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Saxton, J.E.1
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