-
2
-
-
84943388739
-
Pyrroles and Their Benzoderivatives: Synthesis and Applications
-
Katritzky, A. R, Rees, C. W, Eds, Pergamon Press: Oxford, UK
-
(b) Sundberg, R. J. Pyrroles and Their Benzoderivatives: Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, UK, 1984; Vol. 4, pp 313-376.
-
(1984)
Comprehensive Heterocyclic Chemistry
, vol.4
, pp. 313-376
-
-
Sundberg, R.J.1
-
4
-
-
64349095640
-
-
Joule, J. A. Indole and its Derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme Verlag: Stuttgart, Germany, 2000; Category 2, 10, Chapter 10.13.
-
(d) Joule, J. A. Indole and its Derivatives. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Thomas, E. J., Ed.; George Thieme Verlag: Stuttgart, Germany, 2000; Category 2, Vol. 10, Chapter 10.13.
-
-
-
-
5
-
-
0037366605
-
-
(2) Horton, D. A.; Bourne, G. T.; Smyth, M. L. Chem. Rev. 2003, 103, 893-930.
-
(2003)
Chem. Rev
, vol.103
, pp. 893-930
-
-
Horton, D.A.1
Bourne, G.T.2
Smyth, M.L.3
-
6
-
-
0003911273
-
-
MDL Information Systems Inc, San Leandro, CA
-
(3) MDL Drug Data Report; MDL Information Systems Inc.: San Leandro, CA.
-
MDL Drug Data Report
-
-
-
7
-
-
0027461856
-
-
For the activation of indoles with stoichiometric chromium, see: a
-
(4) For the activation of indoles with stoichiometric chromium, see: (a) Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1399-1402.
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 1399-1402
-
-
Semmelhack, M.F.1
Rhee, H.2
-
8
-
-
0027279339
-
-
For the Pd-catalyzed enolate arylations of indoles, see
-
(b) Semmelhack, M. F.; Knochel, P.; Singleton, T. Tetrahedron Lett. 1993, 34, 5051-5054. For the Pd-catalyzed enolate arylations of indoles, see:
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 5051-5054
-
-
Semmelhack, M.F.1
Knochel, P.2
Singleton, T.3
-
9
-
-
23944501763
-
-
(c) MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421-3424.
-
(2005)
Org. Lett
, vol.7
, pp. 3421-3424
-
-
MacKay, J.A.1
Bishop, R.L.2
Rawal, V.H.3
-
10
-
-
25444435181
-
-
(d) Baudoux, J.; Blake, A. J.; Simpkins, N. S. Org. Lett. 2005, 7, 4087-4089.
-
(2005)
Org. Lett
, vol.7
, pp. 4087-4089
-
-
Baudoux, J.1
Blake, A.J.2
Simpkins, N.S.3
-
11
-
-
0006982548
-
-
For reviews regarding heteroaromatic arynes, see: a
-
(5) For reviews regarding heteroaromatic arynes, see: (a) Reinecke, M. G. Tetrahedron 1982, 38, 427-498.
-
(1982)
Tetrahedron
, vol.38
, pp. 427-498
-
-
Reinecke, M.G.1
-
13
-
-
0037415520
-
-
For recent reviews regarding aryne chemistry and synthetic applications, see: a
-
(6) For recent reviews regarding aryne chemistry and synthetic applications, see: (a) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730.
-
(2003)
Tetrahedron
, vol.59
, pp. 701-730
-
-
Pellissier, H.1
Santelli, M.2
-
14
-
-
0037415856
-
-
(b) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem.. Int. Ed. 2003, 42, 502-528.
-
(2003)
Angew. Chem.. Int. Ed
, vol.42
, pp. 502-528
-
-
Wenk, H.H.1
Winkler, M.2
Sander, W.3
-
16
-
-
64349120872
-
-
a
-
(7) (a) Julia, M.; Huang, Y.; Igolen, J. C. R. Acad. Sci. Ser. C 1967, 265, 110-112.
-
(1967)
C. R. Acad. Sci. Ser. C
, vol.265
, pp. 110-112
-
-
Julia, M.1
Huang, Y.2
Igolen, J.3
-
17
-
-
33947097646
-
-
For related studies, see
-
(b) Igolen, J.; Kolb, A. C. R. Acad. Sci., Ser. C 1969, 269, 54-56. For related studies, see:
-
(1969)
C. R. Acad. Sci., Ser. C
, vol.269
, pp. 54-56
-
-
Igolen, J.1
Kolb, A.2
-
18
-
-
64349121365
-
-
(c) Julia, M.; Goffic, F. L.; Igolen, J.; Baillarge, M. C. R. Acad. Sci. Ser. C 1967, 264, 118-120.
-
(1967)
C. R. Acad. Sci. Ser. C
, vol.264
, pp. 118-120
-
-
Julia, M.1
Goffic, F.L.2
Igolen, J.3
Baillarge, M.4
-
19
-
-
64349087507
-
-
(d) Julia, M.; Igolen, J.; Kolb, M. C. R. Acad. Sci. Ser. C 1971, 273, 1776-1777.
-
(1971)
C. R. Acad. Sci. Ser. C
, vol.273
, pp. 1776-1777
-
-
Julia, M.1
Igolen, J.2
Kolb, M.3
-
20
-
-
35548986758
-
-
a
-
(8) (a) Buszek, K. R.; Luo, D.; Kondrashov, M.; Brown, N.; Vander-Velde, D. Org. Lett. 2007, 9, 4135-4137.
-
(2007)
Org. Lett
, vol.9
, pp. 4135-4137
-
-
Buszek, K.R.1
Luo, D.2
Kondrashov, M.3
Brown, N.4
Vander-Velde, D.5
-
21
-
-
56949094234
-
-
(b) Brown, N.; Luo, D.; VanderVelde, D.; Yang, S.; Brassfield, A.; Buszek, K. R. Tetrahedron Lett. 2009, 50, 63-65.
-
(2009)
Tetrahedron Lett
, vol.50
, pp. 63-65
-
-
Brown, N.1
Luo, D.2
VanderVelde, D.3
Yang, S.4
Brassfield, A.5
Buszek, K.R.6
-
22
-
-
59649105471
-
-
(c) Buszek, K. R.; Brown, N.; Luo, D. Org. Lett. 2009, 11, 201-204.
-
(2009)
Org. Lett
, vol.11
, pp. 201-204
-
-
Buszek, K.R.1
Brown, N.2
Luo, D.3
-
23
-
-
64349085214
-
-
Attempts to synthesize 2, 3-indolynes have been met without success; see: (a) Muller, H. Dissertation, University of Heidelberg, 1964.
-
(9) Attempts to synthesize 2, 3-indolynes have been met without success; see: (a) Muller, H. Dissertation, University of Heidelberg, 1964.
-
-
-
-
26
-
-
64349107503
-
-
See also ref 5a
-
See also ref 5a.
-
-
-
-
27
-
-
0037241494
-
-
For the nucleophilicity of N-methylindole, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
-
(10) For the nucleophilicity of N-methylindole, see: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
-
-
-
-
28
-
-
64349094245
-
-
During preparation of this manuscript, Buszek and co-workers reported the synthesis of C3-substituted indolyl silyltriflates using a Fischer indolization strategy; see ref 8b.
-
(11) During preparation of this manuscript, Buszek and co-workers reported the synthesis of C3-substituted indolyl silyltriflates using a Fischer indolization strategy; see ref 8b.
-
-
-
-
29
-
-
0002977163
-
-
(12) Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211-1214.
-
(1983)
Chem. Lett
, vol.12
, pp. 1211-1214
-
-
Himeshima, Y.1
Sonoda, T.2
Kobayashi, H.3
-
30
-
-
64349084069
-
-
Challenges are primarily associated with the acidity of the C2 hydrogen and the electron-rich nature of the indole ring (e.g., undesired reactivity at C3 and propensity to undergo protodesilylation at C4).
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(13) Challenges are primarily associated with the acidity of the C2 hydrogen and the electron-rich nature of the indole ring (e.g., undesired reactivity at C3 and propensity to undergo protodesilylation at C4).
-
-
-
-
33
-
-
64349115340
-
-
5-Hydroxyindoles can also be readily prepared by the classic Nenitzescu indole synthesis; for a review, see: Allen, G. R. Org. React. 1973, 20, 337-454.
-
(15) 5-Hydroxyindoles can also be readily prepared by the classic Nenitzescu indole synthesis; for a review, see: Allen, G. R. Org. React. 1973, 20, 337-454.
-
-
-
-
34
-
-
24144466864
-
-
a
-
(16) (a) Kauch, M.; Snieckus, V.; Hoppe, D. J. Org. Chem. 2005, 70, 7149-7158.
-
(2005)
J. Org. Chem
, vol.70
, pp. 7149-7158
-
-
Kauch, M.1
Snieckus, V.2
Hoppe, D.3
-
36
-
-
0028903040
-
-
For the selective C4 lithiation of a related N-silylated substrate, see: Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484-1485.
-
(17) For the selective C4 lithiation of a related N-silylated substrate, see: Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484-1485.
-
-
-
-
37
-
-
0012397313
-
-
(18) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
-
(1990)
Chem. Rev
, vol.90
, pp. 879-933
-
-
Snieckus, V.1
-
38
-
-
64349098954
-
-
Cleavage of the carbamate of 16 was routinely accompanied by loss of the C4 silyl substituent under a variety of reaction conditions.
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(19) Cleavage of the carbamate of 16 was routinely accompanied by loss of the C4 silyl substituent under a variety of reaction conditions.
-
-
-
-
42
-
-
48849105709
-
-
a
-
(23) (a) Shi, R; Waldo, J. P.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409-2412.
-
(2008)
Org. Lett
, vol.10
, pp. 2409-2412
-
-
Shi, R.1
Waldo, J.P.2
Chen, Y.3
Larock, R.C.4
-
43
-
-
52449098755
-
-
(b) Campbell-Verduyn, L.; Elsinga, P. H.; Mirfeizi, L.; Dierckx, R. A.; Feringa, B. L. Org. Biomol. Chem. 2008, 6, 3461-3463.
-
(2008)
Org. Biomol. Chem
, vol.6
, pp. 3461-3463
-
-
Campbell-Verduyn, L.1
Elsinga, P.H.2
Mirfeizi, L.3
Dierckx, R.A.4
Feringa, B.L.5
-
45
-
-
64349122561
-
-
See the Supporting Informationfor details
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(25) See the Supporting Informationfor details.
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