An efficient synthesis of 3-cyanoquinoline derivatives

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4013-4016

  Charpentier, Patricia ^a   Lobrégat, Virginie ^a   Levacher, Vincent ^a   Dupas, Georges ^a   Quéguiner, Guy ^a   Bourguignon, Jean ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 CYANOQUINOLINE DERIVATIVE; 3,3 DIMETHOXY 2 FORMYLPROPANENITRILE; ANILINE DERIVATIVE; DICHLOROMETHANE; ENAMINE; METHANOL; NITRILE; PYRIDINE; QUINOLINE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; SYNTHESIS;

EID: 0032482517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00677-7     Document Type: Article

References (16)

1. 1. Annulated NADH models in the quinoline, pyridoindole and benzothienopyridine series offer not only the advantage to be more stable over their analogues in pyridine series but also can be used in the presence of strong Lewis or Brönsted acids allowing the reduction of a large range of substrates: Ohno, A.; Ishihara, Y.; Ushida, S.; Oka, S. Tetrahedron Lett. 1982, 23, 3185. Shinkai, S.; Hamada, H.; Kusano, Y.; Manabe, O. J. Chem. Soc. Perkin Trans.II. 1979, 699. Levacher, V.; Boussad, N.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1992, 48, 831-840. Berkous, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Bull. Soc. Chem. Fr. 1994, 131, 632-635.
2. 1. Annulated NADH models in the quinoline, pyridoindole and benzothienopyridine series offer not only the advantage to be more stable over their analogues in pyridine series but also can be used in the presence of strong Lewis or Brönsted acids allowing the reduction of a large range of substrates: Ohno, A.; Ishihara, Y.; Ushida, S.; Oka, S. Tetrahedron Lett. 1982, 23, 3185. Shinkai, S.; Hamada, H.; Kusano, Y.; Manabe, O. J. Chem. Soc. Perkin Trans. II. 1979, 699. Levacher, V.; Boussad, N.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1992, 48, 831-840. Berkous, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Bull. Soc. Chem. Fr. 1994, 131, 632-635.
3. 1. Annulated NADH models in the quinoline, pyridoindole and benzothienopyridine series offer not only the advantage to be more stable over their analogues in pyridine series but also can be used in the presence of strong Lewis or Brönsted acids allowing the reduction of a large range of substrates: Ohno, A.; Ishihara, Y.; Ushida, S.; Oka, S. Tetrahedron Lett. 1982, 23, 3185. Shinkai, S.; Hamada, H.; Kusano, Y.; Manabe, O. J. Chem. Soc. Perkin Trans.II. 1979, 699. Levacher, V.; Boussad, N.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1992, 48, 831-840. Berkous, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Bull. Soc. Chem. Fr. 1994, 131, 632-635.
4. 1. Annulated NADH models in the quinoline, pyridoindole and benzothienopyridine series offer not only the advantage to be more stable over their analogues in pyridine series but also can be used in the presence of strong Lewis or Brönsted acids allowing the reduction of a large range of substrates: Ohno, A.; Ishihara, Y.; Ushida, S.; Oka, S. Tetrahedron Lett. 1982, 23, 3185. Shinkai, S.; Hamada, H.; Kusano, Y.; Manabe, O. J. Chem. Soc. Perkin Trans.II. 1979, 699. Levacher, V.; Boussad, N.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1992, 48, 831-840. Berkous, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Bull. Soc. Chem. Fr. 1994, 131, 632-635.
5. 2. Gurnos, J. The Chemistry of Heterocyclic Compounds; Stonebridge Press, 1977, 32, 93-318.
6. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
7. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
8. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
9. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
10. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
11. 3. For the preparation of quinolines substituted at C-3 by a carboxylic acid or related functionality see: Sakakibara, Y.; Ido, Y.; Sasaki, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778. Jansen, H. E.; Wibaut, J. P. Rec. Trav. Chim. 1937, 56, 709-713. Harris, N. D.; Synthesis 1973, 48-49. Burke, T. R.; Lim, B.; Marquez, V. E.; Li, Z. G.; Bolen, J. B.; Stefanova, I.; Horak, I. D. J. Med. Chem. 1993, 36, 425-432. Uhle, F. C.; Jacobs, W. A. J. Org. Chem. 1945, 10, 76-86. 4. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Synthesis 1987, 1124-1126.
12. 5. Eliel, E. E.; Wilen, S. H. Stereochemistry of Organic Compounds, John Wiley, New York, 1994, pp 544-555.
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