-
1
-
-
0034677697
-
-
(a) Sucheck, S. J.; Greenber, W. A.; Tolbert, T. J.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1080-1084.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 1080-1084
-
-
Sucheck, S.J.1
Greenber, W.A.2
Tolbert, T.J.3
Wong, C.-H.4
-
2
-
-
0034689404
-
-
(b) Bosch, J.; Roca, T.; Perez, C. G.; Montanari, S. Bioorg. Med. Chem. Lett. 2000, 10, 563-566.
-
(2000)
Bioorg. Med. Chem. Lett.
, vol.10
, pp. 563-566
-
-
Bosch, J.1
Roca, T.2
Perez, C.G.3
Montanari, S.4
-
3
-
-
0029095479
-
-
(c) Glase, S. A.; Corbin, A. E.; Pugsley, T. A.; Heffner, T. G.; Wise, L. D. J. Med. Chem. 1995, 38, 3132-3137.
-
(1995)
J. Med. Chem.
, vol.38
, pp. 3132-3137
-
-
Glase, S.A.1
Corbin, A.E.2
Pugsley, T.A.3
Heffner, T.G.4
Wise, L.D.5
-
8
-
-
2142722047
-
-
Hydrogenolysis of other quinoline heterosubstituents (F, OH, OMe) has been reported under similar conditions: Vierhapper, F. W.; Honel, M. J. Chem. Soc., Perkin Trans. 1 1980, 1933-1939.
-
(1980)
J. Chem. Soc., Perkin Trans. 1
, pp. 1933-1939
-
-
Vierhapper, F.W.1
Honel, M.2
-
9
-
-
0005786141
-
-
Vijn, R. J.; Arts, H. J.; Maas, P. J.; Castelijns, A. M. J. Am. Chem. Soc. 1992, 58, 887-891.
-
(1992)
J. Am. Chem. Soc.
, vol.58
, pp. 887-891
-
-
Vijn, R.J.1
Arts, H.J.2
Maas, P.J.3
Castelijns, A.M.4
-
10
-
-
2142835719
-
-
Takeda Chemical Industires Ltd. Japan; PCT Int. Appl. WO 20010211577; JP 2002003370, 2001
-
Kato, K.; Terauchi, J.; Mori, M.; Suzuki, N.; Shimomura, Y.; Takekawa, S.; Ishihara, Y. Takeda Chemical Industires Ltd. Japan; PCT Int. Appl. WO 20010211577; JP 2002003370, 2001.
-
-
-
Kato, K.1
Terauchi, J.2
Mori, M.3
Suzuki, N.4
Shimomura, Y.5
Takekawa, S.6
Ishihara, Y.7
-
11
-
-
0029801534
-
-
Dukat, M.; Fiedler, M.; Dumas, D.; Damaj, I.; Martin, B. R.; Rosecrans, J. A.; James, J. R.; Glennon, R. A Eur. J. Med. Chem. 1996, 31, 875-888.
-
(1996)
A Eur. J. Med. Chem.
, vol.31
, pp. 875-888
-
-
Dukat, M.1
Fiedler, M.2
Dumas, D.3
Damaj, I.4
Martin, B.R.5
Rosecrans, J.A.6
James, J.R.7
Glennon, R.8
-
12
-
-
0017059908
-
-
Adachi, J.; Nomura, K.; Yamamoto, S.-I.; Mitsuhashi, Chem. Pharm. Bull. 1976, 24, 2876-2980.
-
(1976)
Chem. Pharm. Bull.
, vol.24
, pp. 2876-2980
-
-
Adachi, J.1
Nomura, K.2
Yamamoto, S.-I.3
Mitsuhashi4
-
13
-
-
2142728408
-
-
Preparation of 7-amino-5,6,7,8-tetrahydroquinoline via a different route has been described: Cliffe, I. A.; Ifill, A. D.; Mansell, H. L.; Todd, R. S.; White, A. C. Tetrahedron Lett. 1991, 32, 678-692.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 678-692
-
-
Cliffe, I.A.1
Ifill, A.D.2
Mansell, H.L.3
Todd, R.S.4
White, A.C.5
-
14
-
-
0036229349
-
-
Preparation of enantiomerically pure 8-amino-5,6,7,8-tetrahydroquinoline has recently been described: Uenishi, J.; Hamada, M. Synthesis 2002, 5, 625-630.
-
(2002)
Synthesis
, vol.5
, pp. 625-630
-
-
Uenishi, J.1
Hamada, M.2
-
15
-
-
0029122075
-
-
The 1,2,3,4-tetrahydro products 3d, 3e, and 3g are known compounds: (a) Bigge, C. F.; Malone, T. C.; Boxer, P. A.; Nelson, C. B.; Ortwine, D. F.; Schelkun, R. M.; Retz, D. M.; Lescosky, L. J.; Borosky, S. A.; Vartanian, M. G.; Schwarz, R. D.; Campbell, G. W.; Robichaud, L. J.; Watjen, F. J. Med. Chem. 1995, 38, 3720-3740. (b) Reich, S. H.; Fuhry, M. A.; Nguyen, D.; Pino, M. J.; Welsh, K. M.; Webber, S.; Janson, C. A.; Jordan, S. R.; Matthews, D. A.; Smith, W. W.; Bartlett, C. A.; Booth, C. L. J.; Herrmann, S. M.; Howland, E. F.; Morse, C. A.; Ward, R. W.; White, J. J. Med. Chem. 1992, 35, 847-858. (c) Richardson, A.; Amstutz, E. D. J. Org. Chem. 1960, 25, 1138.
-
(1995)
J. Med. Chem.
, vol.38
, pp. 3720-3740
-
-
Bigge, C.F.1
Malone, T.C.2
Boxer, P.A.3
Nelson, C.B.4
Ortwine, D.F.5
Schelkun, R.M.6
Retz, D.M.7
Lescosky, L.J.8
Borosky, S.A.9
Vartanian, M.G.10
Schwarz, R.D.11
Campbell, G.W.12
Robichaud, L.J.13
Watjen, F.14
-
16
-
-
0026589385
-
-
The 1,2,3,4-tetrahydro products 3d, 3e, and 3g are known compounds: (a) Bigge, C. F.; Malone, T. C.; Boxer, P. A.; Nelson, C. B.; Ortwine, D. F.; Schelkun, R. M.; Retz, D. M.; Lescosky, L. J.; Borosky, S. A.; Vartanian, M. G.; Schwarz, R. D.; Campbell, G. W.; Robichaud, L. J.; Watjen, F. J. Med. Chem. 1995, 38, 3720-3740. (b) Reich, S. H.; Fuhry, M. A.; Nguyen, D.; Pino, M. J.; Welsh, K. M.; Webber, S.; Janson, C. A.; Jordan, S. R.; Matthews, D. A.; Smith, W. W.; Bartlett, C. A.; Booth, C. L. J.; Herrmann, S. M.; Howland, E. F.; Morse, C. A.; Ward, R. W.; White, J. J. Med. Chem. 1992, 35, 847-858. (c) Richardson, A.; Amstutz, E. D. J. Org. Chem. 1960, 25, 1138.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 847-858
-
-
Reich, S.H.1
Fuhry, M.A.2
Nguyen, D.3
Pino, M.J.4
Welsh, K.M.5
Webber, S.6
Janson, C.A.7
Jordan, S.R.8
Matthews, D.A.9
Smith, W.W.10
Bartlett, C.A.11
Booth, C.L.J.12
Herrmann, S.M.13
Howland, E.F.14
Morse, C.A.15
Ward, R.W.16
White, J.17
-
17
-
-
2142730955
-
-
The 1,2,3,4-tetrahydro products 3d, 3e, and 3g are known compounds: (a) Bigge, C. F.; Malone, T. C.; Boxer, P. A.; Nelson, C. B.; Ortwine, D. F.; Schelkun, R. M.; Retz, D. M.; Lescosky, L. J.; Borosky, S. A.; Vartanian, M. G.; Schwarz, R. D.; Campbell, G. W.; Robichaud, L. J.; Watjen, F. J. Med. Chem. 1995, 38, 3720-3740. (b) Reich, S. H.; Fuhry, M. A.; Nguyen, D.; Pino, M. J.; Welsh, K. M.; Webber, S.; Janson, C. A.; Jordan, S. R.; Matthews, D. A.; Smith, W. W.; Bartlett, C. A.; Booth, C. L. J.; Herrmann, S. M.; Howland, E. F.; Morse, C. A.; Ward, R. W.; White, J. J. Med. Chem. 1992, 35, 847-858. (c) Richardson, A.; Amstutz, E. D. J. Org. Chem. 1960, 25, 1138.
-
(1960)
J. Org. Chem.
, vol.25
, pp. 1138
-
-
Richardson, A.1
Amstutz, E.D.2
-
18
-
-
2142780159
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
-
Siegel, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, p 438.
-
(1991)
Comprehensive Organic Synthesis
, vol.8
, pp. 438
-
-
Siegel, S.1
-
19
-
-
84986505869
-
-
Chelucci, G.; Cossu, S.; Soccolini, F. J. Heterocycl. Chem. 1986, 23, 1283-1286.
-
(1986)
J. Heterocycl. Chem.
, vol.23
, pp. 1283-1286
-
-
Chelucci, G.1
Cossu, S.2
Soccolini, F.3
-
21
-
-
2142664284
-
-
An alternative, more efficient synthesis of 2n has been reported: Crossley, R.; Curran, A. C. W.; Hill, D. G. J. Chem. Soc., Perkin Trans. 1 1976, 977-982.
-
(1976)
J. Chem. Soc., Perkin Trans. 1
, pp. 977-982
-
-
Crossley, R.1
Curran, A.C.W.2
Hill, D.G.3
-
22
-
-
2142677921
-
-
The 1,2,3,4-tetrahydro products 3j, 3k, 31, and 3m are known compounds: (a) Gogte, V. N.; El-Namaky, H. M.; Salama, M. A.; Tilak, B. D. Tetrahedron Lett. 1969, 39, 3319-3322. (b) Rao, V. A.; Jain, P. C.; Anand, N. Indian J. Chem. 1972, 10, 1134-1135. (c) Rasetti, V.; Rueeger, H.; Maibaum, J.; Mah, R., Gruetter, M.; Cohen, N. C. Ciba-Geigy A.-G., Switzerland. Eur. Pat. Appl. EP 702004, 1996. (d) Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. PCT Int. Appl. WO 9604251, 1996.
-
(1969)
Tetrahedron Lett.
, vol.39
, pp. 3319-3322
-
-
Gogte, V.N.1
El-Namaky, H.M.2
Salama, M.A.3
Tilak, B.D.4
-
23
-
-
2142677921
-
-
The 1,2,3,4-tetrahydro products 3j, 3k, 31, and 3m are known compounds: (a) Gogte, V. N.; El-Namaky, H. M.; Salama, M. A.; Tilak, B. D. Tetrahedron Lett. 1969, 39, 3319-3322. (b) Rao, V. A.; Jain, P. C.; Anand, N. Indian J. Chem. 1972, 10, 1134-1135. (c) Rasetti, V.; Rueeger, H.; Maibaum, J.; Mah, R., Gruetter, M.; Cohen, N. C. Ciba-Geigy A.-G., Switzerland. Eur. Pat. Appl. EP 702004, 1996. (d) Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. PCT Int. Appl. WO 9604251, 1996.
-
(1972)
Indian J. Chem.
, vol.10
, pp. 1134-1135
-
-
Rao, V.A.1
Jain, P.C.2
Anand, N.3
-
24
-
-
2142677921
-
-
Rasetti, V.; Rueeger, H.; Maibaum, J.; Mah, R., Gruetter, M.; Cohen, N. C. Ciba-Geigy A.-G., Switzerland. Eur. Pat. Appl. EP 702004, 1996
-
The 1,2,3,4-tetrahydro products 3j, 3k, 31, and 3m are known compounds: (a) Gogte, V. N.; El-Namaky, H. M.; Salama, M. A.; Tilak, B. D. Tetrahedron Lett. 1969, 39, 3319-3322. (b) Rao, V. A.; Jain, P. C.; Anand, N. Indian J. Chem. 1972, 10, 1134-1135. (c) Rasetti, V.; Rueeger, H.; Maibaum, J.; Mah, R., Gruetter, M.; Cohen, N. C. Ciba-Geigy A.-G., Switzerland. Eur. Pat. Appl. EP 702004, 1996. (d) Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. PCT Int. Appl. WO 9604251, 1996.
-
-
-
-
25
-
-
2142677921
-
-
Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. PCT Int. Appl. WO 9604251, 1996
-
The 1,2,3,4-tetrahydro products 3j, 3k, 31, and 3m are known compounds: (a) Gogte, V. N.; El-Namaky, H. M.; Salama, M. A.; Tilak, B. D. Tetrahedron Lett. 1969, 39, 3319-3322. (b) Rao, V. A.; Jain, P. C.; Anand, N. Indian J. Chem. 1972, 10, 1134-1135. (c) Rasetti, V.; Rueeger, H.; Maibaum, J.; Mah, R., Gruetter, M.; Cohen, N. C. Ciba-Geigy A.-G., Switzerland. Eur. Pat. Appl. EP 702004, 1996. (d) Oku, T.; Kayakiri, H.; Satoh, S.; Abe, Y.; Sawada, Y.; Inoue, T.; Tanaka, H. PCT Int. Appl. WO 9604251, 1996.
-
-
-
-
26
-
-
0034303638
-
-
Methyl 5-carboxylate-5,6,7,8-tetrahydroisoquinoline was prepared via this method: Paivio, E.; Berner, M.; Tolvanen, A.; Jokela, R. Heterocycles 2000, 53, 2241-2246.
-
(2000)
Heterocycles
, vol.53
, pp. 2241-2246
-
-
Paivio, E.1
Berner, M.2
Tolvanen, A.3
Jokela, R.4
-
27
-
-
0000945469
-
-
For a detailed discussion on the mechanism of quinoline hydrogenation see: Okazaki, H.; Onishi, K.; Soeda, M.; Ikefuji, Y.; Tamura, R.; Mochida, I. Bull. Chem. Soc. Jpn. 1990, 63, 3167-3174; refs 4 and 3c.
-
(1990)
Bull. Chem. Soc. Jpn.
, vol.63
, pp. 3167-3174
-
-
Okazaki, H.1
Onishi, K.2
Soeda, M.3
Ikefuji, Y.4
Tamura, R.5
Mochida, I.6
-
28
-
-
0000945469
-
-
refs 4 and 3c
-
For a detailed discussion on the mechanism of quinoline hydrogenation see: Okazaki, H.; Onishi, K.; Soeda, M.; Ikefuji, Y.; Tamura, R.; Mochida, I. Bull. Chem. Soc. Jpn. 1990, 63, 3167-3174; refs 4 and 3c.
-
-
-
-
29
-
-
0015581293
-
-
Bailey, Denis M.; DeGrazia, C. George; Lape, Harlan E.; Frering, Richard; Fort, Dorothy; Skulan, Thomas. J. Med. Chem. 1973, 16, 151-156.
-
(1973)
J. Med. Chem.
, vol.16
, pp. 151-156
-
-
Bailey, D.M.1
DeGrazia, G.C.2
Lape, H.E.3
Frering, R.4
Fort, D.5
Skulan, T.6
-
30
-
-
2142787796
-
-
note
-
The authors acknowledge this, stating "The synthetic possibilities are severely diminished by this hydrogenolysis"; ref 4.
-
-
-
-
33
-
-
0026589721
-
-
Keegstra, M. A.; Peters, T. H. A.; Brandsma, L. Tetrahedron 1992, 48, 3633-3652.
-
(1992)
Tetrahedron
, vol.48
, pp. 3633-3652
-
-
Keegstra, M.A.1
Peters, T.H.A.2
Brandsma, L.3
|