-
1
-
-
2342616654
-
-
For leading references to the physiological activity of indole derivatives, see: (a) Kam, T.-S.; Choo, Y.-M. Helv. Chim. Acta 2004, 87, 991.
-
(2004)
Helv. Chim. Acta
, vol.87
, pp. 991
-
-
Kam, T.-S.1
Choo, Y.-M.2
-
2
-
-
17044375054
-
-
(b) Kuethe, J. T.; Wong, A.; Qu, C.; Smitrovich, J.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2005, 70, 2555.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2555
-
-
Kuethe, J.T.1
Wong, A.2
Qu, C.3
Smitrovich, J.4
Davies, I.W.5
Hughes, D.L.6
-
3
-
-
20944432343
-
-
(c) Van Zandt, M. C.; Jones, M. L.; Gunn, D. E.; Geraci, L. S.; Jones, J. H.; Sawicki, D. R.; Sredy, J.; Jacot, J. L.; DiCioccio, A. T.; Petrova, T.; Mitschler, A.; Podjarny, A. D. J. Med. Chem. 2005, 48, 3141.
-
(2005)
J. Med. Chem.
, vol.48
, pp. 3141
-
-
Van Zandt, M.C.1
Jones, M.L.2
Gunn, D.E.3
Geraci, L.S.4
Jones, J.H.5
Sawicki, D.R.6
Sredy, J.7
Jacot, J.L.8
DiCioccio, A.T.9
Petrova, T.10
Mitschler, A.11
Podjarny, A.D.12
-
4
-
-
0033544422
-
-
For leading references to current applications of the Fischer indole synthesis, see: Wagaw, S.; Yang, B. Y.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10251
-
-
Wagaw, S.1
Yang, B.Y.2
Buchwald, S.L.3
-
6
-
-
0037176253
-
-
For more recent references, see: (b) Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 15168
-
-
Rutherford, J.L.1
Rainka, M.P.2
Buchwald, S.L.3
-
7
-
-
0037009015
-
-
(c) Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 3230
-
-
Kamijo, S.1
Yamamoto, Y.2
-
8
-
-
0037122126
-
-
(d) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2002, 41, 4732.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4732
-
-
Arisawa, M.1
Terada, Y.2
Nakagawa, M.3
Nishida, A.4
-
9
-
-
0038682516
-
-
(e) Smith, A. B.; Kanoh, N.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 8228
-
-
Smith, A.B.1
Kanoh, N.2
Ishiyama, H.3
Minakawa, N.4
Rainier, J.D.5
Hartz, R.A.6
Cho, Y.S.7
Cui, H.8
Moser, W.H.9
-
10
-
-
0042808535
-
-
(f) Siebeneicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3042
-
-
Siebeneicher, H.1
Bytschkov, I.2
Doye, S.3
-
11
-
-
4344572110
-
-
(g) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10546
-
-
Shimada, T.1
Nakamura, I.2
Yamamoto, Y.3
-
12
-
-
12344275854
-
-
(h) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 403
-
-
Willis, M.C.1
Brace, G.N.2
Holmes, I.P.3
-
13
-
-
13244291528
-
-
(i) Baran, P. S.; Guerrero, C. A.; Ambhaikar, N. B.; Hafensteiner, B. D. Angew. Chem., Int. Ed. 2005, 44, 606.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 606
-
-
Baran, P.S.1
Guerrero, C.A.2
Ambhaikar, N.B.3
Hafensteiner, B.D.4
-
16
-
-
0001764817
-
-
There have been scattered reports of the rearrangement of aryl azirines to indoles: (a) Padwa, A.; Smolanoff, J.; Tremper, A. J. Org. Chem. 1976, 41, 543.
-
(1976)
J. Org. Chem.
, vol.41
, pp. 543
-
-
Padwa, A.1
Smolanoff, J.2
Tremper, A.3
-
17
-
-
37049113109
-
-
(b) Isomura, K.; Ayabe, G.; Hatano, S.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 1252.
-
(1980)
J. Chem. Soc., Chem. Commun.
, pp. 1252
-
-
Isomura, K.1
Ayabe, G.2
Hatano, S.3
Taniguchi, H.4
-
18
-
-
0009950509
-
-
(c) Russell, G. A.; Yao, C.-F.; Tashtoush, H. I.; Russell, J. E.; Dedolph, D. F. J. Org. Chem. 1991, 56, 663.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 663
-
-
Russell, G.A.1
Yao, C.-F.2
Tashtoush, H.I.3
Russell, J.E.4
Dedolph, D.F.5
-
21
-
-
37049110899
-
-
(f) For Pd catalysis, see: Isomura, K.; Uto, K.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1977, 664.
-
(1977)
J. Chem. Soc., Chem. Commun.
, pp. 664
-
-
Isomura, K.1
Uto, K.2
Taniguchi, H.3
-
24
-
-
0033543625
-
-
For recent uses of the Neber reaction, see: (a) Chung, J. Y. L.; Ho, G.-J.; Chartrain, M.; Roberge, C.; Zhao, D.; Leazer, J.; Fair, R.; Robbins, M.; Emerson, K.; Mathre, D. J.; McNamara, J. M.; Hughes, D. L.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1999, 40, 6739.
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 6739
-
-
Chung, J.Y.L.1
Ho, G.-J.2
Chartrain, M.3
Roberge, C.4
Zhao, D.5
Leazer, J.6
Fair, R.7
Robbins, M.8
Emerson, K.9
Mathre, D.J.10
McNamara, J.M.11
Hughes, D.L.12
Grabowski, E.J.J.13
Reider, P.J.14
-
25
-
-
13844306889
-
-
(b) Sakai, T.; Liu. Y.; Ohta, H.; Korenaga, T.; Ema, T. J. Org. Chem. 2005, 70, 1369.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 1369
-
-
Sakai, T.1
Liu, Y.2
Ohta, H.3
Korenaga, T.4
Ema, T.5
-
26
-
-
17744378379
-
-
Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5970.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 5970
-
-
Garg, N.K.1
Caspi, D.D.2
Stoltz, B.M.3
-
27
-
-
0001677467
-
-
For alternative procedures for the preparation of azirines from α-aryl ketones, see: Barcus, R. L.; Hadel, L. M.; Johnston, L. J.; Platz, M. S.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 3928. In our hands, these procedures were not as efficient as those that we report here.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3928
-
-
Barcus, R.L.1
Hadel, L.M.2
Johnston, L.J.3
Platz, M.S.4
Savino, T.G.5
Scaiano, J.C.6
-
28
-
-
31944434448
-
-
The cyclodehydration of the oxime of an α-aryl ketone to give the indole is a goal that dates back at least 50 years: Loffler, A.; Ginsburg, D. Nature 1953, 172, 820. Our experience with the oximes of α-aryl ketones that we have studied is that they sometimes sublime on heating under reduced pressure, but they do not give even traces of indole.
-
(1953)
Nature
, vol.172
, pp. 820
-
-
Loffler, A.1
Ginsburg, D.2
-
29
-
-
0001694061
-
-
Several of the substances reported here were previously described, (a) 5c: Padwa, A.; Rosenthal, R. J.; Dent, W.; Filho, P.; Turro, N. J.; Hrovat, D. A.; Could, I. R. J. Org. Chem. 1984, 49, 3174.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 3174
-
-
Padwa, A.1
Rosenthal, R.J.2
Dent, W.3
Filho, P.4
Turro, N.J.5
Hrovat, D.A.6
Could, I.R.7
-
31
-
-
0000612008
-
-
(c) 15: Katritzky, A. R.; Toader, D.; Xie, L. J. Org. Chem. 1996, 61, 7571.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7571
-
-
Katritzky, A.R.1
Toader, D.2
Xie, L.3
-
32
-
-
37049075499
-
-
(d) 16: Baccolini, G.; Dalpozwi, R.; Todesco, P. E. J. Chem. Soc., Perkin Trans. 1 1988, 971.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 971
-
-
Baccolini, G.1
Dalpozwi, R.2
Todesco, P.E.3
-
33
-
-
31944443660
-
-
U.S. Patent 6,861,444 B2, 2005
-
(e) 17: Ikuta, S.; Shiro, M.; Ogawa, K. U.S. Patent 6,861,444 B2, 2005.
-
-
-
Ikuta, S.1
Shiro, M.2
Ogawa, K.3
|