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Volumn 67, Issue 22, 2002, Pages 7890-7893

Concise preparation of amino-5,6,7,8-tetrahydroquinolines and amino-5,6,7,8-tetrahydroisoquinolines via catalytic hydrogenation of acetamidoquinolines and acetamidoisoquinolines

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVE REDUCTION;

EID: 0036828173     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026258k     Document Type: Article
Times cited : (33)

References (33)
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    • 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
  • 17
    • 2142730955 scopus 로고
    • 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 scopus 로고
    • 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
  • 22
    • 2142677921 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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.
  • 28
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    • 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.
  • 30
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    • note
    • The authors acknowledge this, stating "The synthetic possibilities are severely diminished by this hydrogenolysis"; ref 4.


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