-
1
-
-
33746864043
-
-
For reviews of indole syntheses, see: a
-
For reviews of indole syntheses, see: (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
-
(2006)
Chem. Rev.
, vol.106
, pp. 2875
-
-
Humphrey, G.R.1
Kuethe, J.T.2
-
7
-
-
33947482239
-
-
For reviews, see: a
-
For reviews, see: (a) Robinson, B. Chem. Rev. 1963, 63, 373.
-
(1963)
Chem. Rev.
, vol.63
, pp. 373
-
-
Robinson, B.1
-
10
-
-
32644448312
-
-
For selected examples utilizing catalytic amounts of Lewis acids, see: a ZnCl2
-
For selected examples utilizing catalytic amounts of Lewis acids, see: (a) ZnCl2: Lipinska, T. M.; Czarnocki, S. J. Org Lett. 2006, 8, 367.
-
(2006)
J. Org Lett.
, vol.8
, pp. 367
-
-
Lipinska, T.M.1
Czarnocki, S.2
-
11
-
-
70449688166
-
-
3
-
3: Srinivasa, A.; Mahadevan, K. M.; Varma, P. P.; Sudhakara, A. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 1843.
-
(2009)
Phosphorus, Sulfur Silicon Relat. Elem.
, vol.184
, pp. 1843
-
-
Srinivasa, A.1
Mahadevan, K.M.2
Varma, P.P.3
Sudhakara, A.4
-
12
-
-
69249233597
-
-
2O
-
2O: Sudhakara, A.; Jayadevappa, H.; Kumar, H. N. H.; Mahadevan, K. M. Lett. Org. Chem. 2009, 6, 159.
-
(2009)
Lett. Org. Chem.
, vol.6
, pp. 159
-
-
Sudhakara, A.1
Jayadevappa, H.2
Kumar, H.N.H.3
Mahadevan, K.M.4
-
13
-
-
57449105151
-
-
(d) Varma, P. P.; Sherigara, B. S.; Mahadevan, K. M.; Hulikal, V. Synth. Commun. 2009, 39, 158.
-
(2009)
Synth. Commun.
, vol.39
, pp. 158
-
-
Varma, P.P.1
Sherigara, B.S.2
Mahadevan, K.M.3
Hulikal, V.4
-
14
-
-
77951793871
-
-
For selected recent examples of indolenine syntheses using the Fischer indolization, see: a
-
For selected recent examples of indolenine syntheses using the Fischer indolization, see: (a) Sajjadifar, S.; Vahedi, H.; Massoudi, A.; Louie, O. Molecules 2010, 15, 2491.
-
(2010)
Molecules
, vol.15
, pp. 2491
-
-
Sajjadifar, S.1
Vahedi, H.2
Massoudi, A.3
Louie, O.4
-
16
-
-
33846273472
-
-
For an elegant application in total synthesis, see
-
(c) Liu, K. G.; Robichaud, A. J.; Lo, J. R.; Mattes, J. F.; Cai, Y. Org. Lett. 2006, 8, 5769. For an elegant application in total synthesis, see:
-
(2006)
Org. Lett.
, vol.8
, pp. 5769
-
-
Liu, K.G.1
Robichaud, A.J.2
Lo, J.R.3
Mattes, J.F.4
Cai, Y.5
-
18
-
-
0037159759
-
-
For representative examples, see: a
-
For representative examples, see: (a) Tsuji, R.; Nakagawa, M.; Nishida, A. Heterocycles 2002, 58, 587.
-
(2002)
Heterocycles
, vol.58
, pp. 587
-
-
Tsuji, R.1
Nakagawa, M.2
Nishida, A.3
-
19
-
-
0000353442
-
-
(b) Takano, S.; Moriya, M.; Iwabuchi, Y.; Ogasawara, K. Chem. Lett. 1990, 109.
-
(1990)
Chem. Lett.
, pp. 109
-
-
Takano, S.1
Moriya, M.2
Iwabuchi, Y.3
Ogasawara, K.4
-
21
-
-
0012779411
-
-
(d) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631.
-
(1971)
Tetrahedron
, vol.27
, pp. 5631
-
-
Britten, A.Z.1
Bardsley, W.G.2
Hill, C.M.3
-
22
-
-
0014213317
-
-
(e) Grandberg, I. I.; Zuyanova, T. I.; Afonina, N. I.; Ivanova, T. A. Dokl. Akad. Nauk SSSR 1967, 176, 583.
-
(1967)
Dokl. Akad. Nauk SSSR
, vol.176
, pp. 583
-
-
Grandberg, I.I.1
Zuyanova, T.I.2
Afonina, N.I.3
Ivanova, T.A.4
-
23
-
-
33646872644
-
-
Nishida, A.; Ushigome, S.; Sugimoto, A.; Arai, S. Heterocycles 2005, 66, 181.
-
(2005)
Heterocycles
, vol.66
, pp. 181
-
-
Nishida, A.1
Ushigome, S.2
Sugimoto, A.3
Arai, S.4
-
24
-
-
68149176713
-
-
Boal, B. W.; Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458.
-
(2009)
Org. Lett.
, vol.11
, pp. 3458
-
-
Boal, B.W.1
Schammel, A.W.2
Garg, N.K.3
-
25
-
-
77954243268
-
-
Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N. K. Tetrahedron 2010, 66, 4687.
-
(2010)
Tetrahedron
, vol.66
, pp. 4687
-
-
Schammel, A.W.1
Boal, B.W.2
Zu, L.3
Mesganaw, T.4
Garg, N.K.5
-
26
-
-
41649095459
-
-
For a review, see
-
For a review, see: Knölker, H.-J.; Reddy, K. R. Alkaloids (San Diego) 2008, 65, 181.
-
(2008)
Alkaloids (San Diego)
, vol.65
, pp. 181
-
-
Knölker, H.-J.1
Reddy, K.R.2
-
27
-
-
4644335310
-
-
For selected examples, see: a Baeyer-Villiger oxidations
-
For selected examples, see: (a) Baeyer-Villiger oxidations: Reetz, M. T.; Brunner, B.; Schneider, T.; Schulz, F.; Clouthier, C. M.; Kayser, M. M. Angew. Chem., Int. Ed. 2004, 43, 4075.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 4075
-
-
Reetz, M.T.1
Brunner, B.2
Schneider, T.3
Schulz, F.4
Clouthier, C.M.5
Kayser, M.M.6
-
28
-
-
83055186601
-
-
Angew. Chem. 2004, 116, 4167.
-
(2004)
Angew. Chem.
, vol.116
, pp. 4167
-
-
-
29
-
-
33846910216
-
-
Aldol reactions
-
(b) Aldol reactions: Jiang, J.; Luo, S.-W.; Cun, L.-F.; Gong, L.-Z. Chem. Commun. 2007, 736.
-
(2007)
Chem. Commun.
, pp. 736
-
-
Jiang, J.1
Luo, S.-W.2
Cun, L.-F.3
Gong, L.-Z.4
-
30
-
-
36648999792
-
-
Michael additions
-
(c) Michael additions: Sanzhong, L.; Zhang, L.; Mi, X.; Qiao, Y.; Cheng, J.-P. J. Org. Chem. 2007, 72, 9350.
-
(2007)
J. Org. Chem.
, vol.72
, pp. 9350
-
-
Sanzhong, L.1
Zhang, L.2
Mi, X.3
Qiao, Y.4
Cheng, J.-P.5
-
31
-
-
79958831362
-
-
Ring expansions with diazoacetates
-
(d) Ring expansions with diazoacetates: Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2011, 133, 8834.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 8834
-
-
Hashimoto, T.1
Naganawa, Y.2
Maruoka, K.3
-
33
-
-
80054744159
-
-
See also: Ren, L.; Lei, T.; Gong, L.-Z. Chem. Commun. 2011, 47, 11683.
-
(2011)
Chem. Commun.
, vol.47
, pp. 11683
-
-
Ren, L.1
Lei, T.2
Gong, L.-Z.3
-
34
-
-
77953261329
-
-
For reviews of chiral phosphoric acid catalysis, see: a
-
For reviews of chiral phosphoric acid catalysis, see: (a) Terada, M. Synthesis 2010, 1929.
-
(2010)
Synthesis
, pp. 1929
-
-
Terada, M.1
-
35
-
-
77950248809
-
-
(b) Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395.
-
(2010)
Top. Curr. Chem.
, vol.291
, pp. 395
-
-
Kampen, D.1
Reisinger, C.M.2
List, B.3
-
37
-
-
47849090006
-
-
For examples of enantioselective 3, 3-sigmatropic rearrangements catalyzed by chiral Brønsted acids, see: a
-
For examples of enantioselective [3, 3]-sigmatropic rearrangements catalyzed by chiral Brønsted acids, see: (a) Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 9228.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 9228
-
-
Uyeda, C.1
Jacobsen, E.N.2
-
38
-
-
57749121489
-
-
(b) Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2008, 47, 10090.
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 10090
-
-
Rueping, M.1
Antonchick, A.P.2
-
39
-
-
58549102018
-
-
Angew. Chem. 2008, 120, 10244.
-
(2008)
Angew. Chem.
, vol.120
, pp. 10244
-
-
-
40
-
-
78650152343
-
-
(c) Uyeda, C.; Rötheli, A. R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 9753.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 9753
-
-
Uyeda, C.1
Rötheli, A.R.2
Jacobsen, E.N.3
-
41
-
-
83055186600
-
-
Angew. Chem. 2010, 122, 9947.
-
(2010)
Angew. Chem.
, vol.122
, pp. 9947
-
-
-
43
-
-
77954595168
-
-
For selected examples, see: a
-
For selected examples, see: (a) Yamada, S.; Chibata, I.; Tsurui, R. Pharm. Bull. 1953, 1, 14.
-
(1953)
Pharm. Bull.
, vol.1
, pp. 14
-
-
Yamada, S.1
Chibata, I.2
Tsurui, R.3
-
44
-
-
77951205995
-
-
(b) Wahab, B.; Ellames, G.; Passey, S.; Watts, P. Tetrahedron 2010, 66, 3861.
-
(2010)
Tetrahedron
, vol.66
, pp. 3861
-
-
Wahab, B.1
Ellames, G.2
Passey, S.3
Watts, P.4
-
45
-
-
0012177920
-
-
For a review of heterogeneous catalysis of the Fischer indole synthesis, see:, Sheldon, R. A., Bekkum, H., Eds.; Wiley-VCH: New York
-
(c) For a review of heterogeneous catalysis of the Fischer indole synthesis, see: Downing, R. S.; Kunkeler, P. J. In Fine Chemicals through Heterogeneous Catalysis; Sheldon, R. A., Bekkum, H., Eds.; Wiley-VCH: New York, 2001; pp 178-183.
-
(2001)
Fine Chemicals Through Heterogeneous Catalysis
, pp. 178-183
-
-
Downing, R.S.1
Kunkeler, P.J.2
-
46
-
-
78650359625
-
-
SPINOL-derived phosphoric acids were independently introduced by three research groups. See: a
-
SPINOL-derived phosphoric acids were independently introduced by three research groups. See: (a) Xu, F.; Huang, D.; Han, C.; Shen, W.; Lin, X.; Wang, Y. J. Org Chem. 2010, 75, 8677.
-
(2010)
J. Org Chem.
, vol.75
, pp. 8677
-
-
Xu, F.1
Huang, D.2
Han, C.3
Shen, W.4
Lin, X.5
Wang, Y.6
-
47
-
-
77953892916
-
-
(b) Coric, I.; Müller, S.; List, B. J. Am. Chem. Soc. 2010, 132, 8536.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 8536
-
-
Coric, I.1
Müller, S.2
List, B.3
-
48
-
-
79956136230
-
-
(c) Xing, C.-H.; Liao, Y.-X.; Ng, J.; Hu, Q.-S. J. Org. Chem. 2011, 76, 4125.
-
(2011)
J. Org. Chem.
, vol.76
, pp. 4125
-
-
Xing, C.-H.1
Liao, Y.-X.2
Ng, J.3
Hu, Q.-S.4
-
49
-
-
78449300334
-
-
For an example of a study showing how varying N-benzyl groups in tetrahydrocarbazoles affects the biological activity, see
-
For an example of a study showing how varying N-benzyl groups in tetrahydrocarbazoles affects the biological activity, see: Li, L.; Beaulieu, C.; Carriere, M.-C.; Denis, D.; Greig, G.; Guay, D.; O'Neill, G.; Zamboni, R.; Wang, Z. Bioorg. Med. Chem. Lett. 2010, 20, 7462.
-
(2010)
Bioorg. Med. Chem. Lett.
, vol.20
, pp. 7462
-
-
Li, L.1
Beaulieu, C.2
Carriere, M.-C.3
Denis, D.4
Greig, G.5
Guay, D.6
O'Neill, G.7
Zamboni, R.8
Wang, Z.9
-
50
-
-
83055176441
-
-
For examples of biologically active 3-aminotetrahydrocarbazoles, see: a, EP 0242518
-
For examples of biologically active 3-aminotetrahydrocarbazoles, see: (a) Böshagen, H.; Rosentreter, U.; Lieb, F.; Oediger, H.; Seuter, F.; Perzborn, E.; Fiedler, V.-B. Cycloalkano[1, 2-b]indole-sulfonamides. EP 0242518, 1987.
-
(1987)
Cycloalkano[1, 2-b]indole-sulfonamides
-
-
Böshagen, H.1
Rosentreter, U.2
Lieb, F.3
Oediger, H.4
Seuter, F.5
Perzborn, E.6
Fiedler, V.-B.7
-
53
-
-
0040514484
-
-
The mechanism was originally proposed by Robinson. See
-
The mechanism was originally proposed by Robinson. See: Robinson, G. M.; Robinson, R. J. Chem. Soc., Trans. 1924, 125, 827.
-
(1924)
J. Chem. Soc., Trans.
, vol.125
, pp. 827
-
-
Robinson, G.M.1
Robinson, R.2
-
54
-
-
79954467842
-
-
Garg and Houk have recently shown that in certain Fischer indolizations, hydrazones without a protecting group can be protonated at either of the two nitrogen atoms, resulting in two different reaction pathways., resulting in two different reaction pathways
-
Garg and Houk have recently shown that in certain Fischer indolizations, hydrazones without a protecting group can be protonated at either of the two nitrogen atoms, resulting in two different reaction pathways., resulting in two different reaction pathways. See: Celebi-Ölcüm, N.; Boal, B. W.; Huters, A. D.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 5752.
-
(2011)
J. Am. Chem. Soc.
, vol.133
, pp. 5752
-
-
Celebi-Ölcüm, N.1
Boal, B.W.2
Huters, A.D.3
Garg, N.K.4
Houk, K.N.5
-
55
-
-
84985448035
-
-
For a discussion of the dependence of the rate-determining step on the acidity of the medium in Fischer indolizations, see
-
For a discussion of the dependence of the rate-determining step on the acidity of the medium in Fischer indolizations, see: Hughes, D. L. J. Phys. Org. Chem. 1994, 7, 625.
-
(1994)
J. Phys. Org. Chem.
, vol.7
, pp. 625
-
-
Hughes, D.L.1
-
56
-
-
0024306565
-
-
Rosentreter, U.; Böshagen, H.; Seuter, F.; Perzborn, E.; Fiedler, V. B. Arzneim. Forsch. 1989, 39, 1519.
-
(1989)
Arzneim. Forsch.
, vol.39
, pp. 1519
-
-
Rosentreter, U.1
Böshagen, H.2
Seuter, F.3
Perzborn, E.4
Fiedler, V.B.5
|