A simple strategy for the preparation of 4-aminoquinolines from β-functionalized enamines

Tetrahedron

Volumn 54, Issue 8, 1998, Pages 1647-1656

  Palacios, Francisco ^a   Aparicio, Domitila ^a   García, Jesús ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; ENAMINE; PHOSPHAZENE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; TECHNIQUE;

EID: 0032546064     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10372-6     Document Type: Article

References (35)

1. 1. For a reviews see: Palacios, F.; Aparicio, D.; Rubiales, G.; Ochoa de Retana, A.; Martínez de Marigorta, E. in "Targets in Heterocyclic Systems. Chemistry and Properties". Attanasi, O.A.; Spinelli, D.; Eds. Italian Chemical Society, Roma, Vol. 1, 1997 (in press).
2. 2. Ebetino, F.F.; Wright, G. C. French Patent 1,388,756 (1965). Chem. Abstr. 1965, 63, 589.
3. 3. Galanakis, D.; Calder, J. A. D.; Ganellin, C. R.; Owen, C. S.; Dunn, P. M. J. Med. Chem. 1995, 38, 3536.
4. 4. a) O'Neill, P. M.; Willock, D. J.; Hawley, S. R.; Bray, P. G.; Storr, R. C.; Ward, S. A.; Park, B. K. J. Med. Chem. 1997, 40, 437.
5. b) Ismail, F. M.; Dascombe, M.J.; Carr, P.; North, S. E. J. Pharm. Pharmacol. 1996, 48, 841.
6. c) Bray, P. G.; Hawley, S. R.; Ward, S. A. Mol. Pharmacol. 1996, 50, 1551.
7. d) Koh, H. L.; Go, M. L.; Ngiam, T. L.; Mak, J. W. Eur. J. Med. Chem. 1994, 29, 107.
8. 5. Ife, R. F.; Brown, T. H.; Keeling, D. J.; Leach, C. A.; Meeson, M. L.; Persons, M. E.; Reavill, D. R.; Theobald, C. J.; Wiggall, K. J. J. Med. Chem. 1992, 35, 3413.
9. b) Ife, R. J. Drugs of the Future 1992, 17, 796.
10. 6. a) Mobilio, D.; Musser, J. H. U.S. Patent 5,216,165 (1993). Chem. Abstr. 1994, 120, 106792.
11. b) El-Azzouny, A. A.; El-Shabrawy, O. A.; El-Azzouny, M. M., Ebeid, M. Y.; Lehmann, J. Sci. Pharm. 1995, 63, 81. Lanza, T. J.; Durette, P. L.; Rollins, T.; Siciliano, S.; Cianciasulo, D. N.; Kobayashi, S. V.; Caldwell, C. G.; Springer, M. S.; Hagman, W. K. J. Med. Chem. 1992, 35, 252.
12. b) El-Azzouny, A. A.; El-Shabrawy, O. A.; El-Azzouny, M. M., Ebeid, M. Y.; Lehmann, J. Sci. Pharm. 1995, 63, 81. Lanza, T. J.; Durette, P. L.; Rollins, T.; Siciliano, S.; Cianciasulo, D. N.; Kobayashi, S. V.; Caldwell, C. G.; Springer, M. S.; Hagman, W. K. J. Med. Chem. 1992, 35, 252.
13. c) Sundquist, W.I.; Bancroft, D. P.; Lippard, S. J. J. Am. Chem., Soc. 1990, 112, 1590.
14. d) Campbell, Hardstone, J. D.; Palmer, M. J. J. Med. Chem. 1988, 31, 1031.
15. e) Kireev, D. B.; Chretien, J. R.; Raevsky, D. A. Eur. J. Med. Chem. 1995, 30, 395.
16. f) Sarges, R.; Gallagher, A.; Chambers, T. J.; Yen, L. A. J. Med. Chem 1993, 36, 2828.. Leach, C. A.; Brown, T. H.; Ife, R. F.; Keeling, D. J.; Laing, S.M.; Persons, M. E.; Price, C. A.; Wiggall, K. J. J. Med. Chem. 1992, 35, 1845.
17. f) Sarges, R.; Gallagher, A.; Chambers, T. J.; Yen, L. A. J. Med. Chem 1993, 36, 2828.. Leach, C. A.; Brown, T. H.; Ife, R. F.; Keeling, D. J.; Laing, S.M.; Persons, M. E.; Price, C. A.; Wiggall, K. J. J. Med. Chem. 1992, 35, 1845.
18. 7. Toy, A. D. F.; Walsh, E. N. In "Phosphorus Chemistry in Everyday Living". American Chemical Society, Washington D. C., 1987. Engel, R. in "Handbook of Organophosphorus Chemistry". M. Dekker Inc., New York, 1992.
19. 7. Toy, A. D. F.; Walsh, E. N. In "Phosphorus Chemistry in Everyday Living". American Chemical Society, Washington D. C., 1987. Engel, R. in "Handbook of Organophosphorus Chemistry". M. Dekker Inc., New York, 1992.
20. 8. For excellent reviews, see: Jones, G. In "Comprehensive Heterocyclic Chemistry"; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, p. 395. Grundon, M. F. In "Alkaloids, Chemical and Biological Perspectives"; Pelletier, S.W., Ed.; Wiley: New York, 1988; Vol. 6, p. 339.
21. 8. For excellent reviews, see: Jones, G. In "Comprehensive Heterocyclic Chemistry"; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, p. 395. Grundon, M. F. In "Alkaloids, Chemical and Biological Perspectives"; Pelletier, S.W., Ed.; Wiley: New York, 1988; Vol. 6, p. 339.
22. 9. For recent contributions see: a) Andersen, K. E.; Lundt, B. F.; Jørgensen, A. S.; Braestrup, C. Eur. J. Med. Chem. 1996, 31, 417.
23. b) Galanakis, D.; Davis, C. A.; Del Rey Herrero, B.; Ganellin, C. R.; Dunn, P. M.; Jenkinson, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 559.
24. 10. Palacios, F.; Aparicio, D.; García, J. Tetrahedron 1997, 53, 2931.
25. 11. For a review see: Barluenga J.; Palacios, F. Org. Prep. Proc. Int. 1991, 23, 1.
26. 12. For a recent contribution see: Palacios, F.; Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146.
27. 13. a) Palacios, F.; Pagalday, J.; Piquet, V.; Dahan, F.; Baceiredo, A.; Bertrand, G. J. Org. Chem. 1997, 62, 292.
28. b) Palacios, F.; García, J.; Ochoa de Retana, A.; Oyarzabal, J. Heterocycles 1995, 41, 1915.
29. 14. Palacios, F.; Aparicio, D.; García, J. Tetrahedron 1996, 52, 9609.
30. 15. Brandsma, L.; Verkruijsse H. D. In "Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratory Manual"; Elsevier, Amsterdam, 1981; p. 199.
31. 16. a) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
32. b) Barluenga, J.; Merino, I.; Palacios, F. J. Chem. Soc., Perkin Trans I 1991, 341.
33. c) Duncan, M.; Gallagher, M. J. Org. Mag. Res. 1981, 15, 37.
34. 17. Schweizer, E. E.; Goff, S. D.; Murray, W.P. J. Org. Chem. 1977, 42, 200.
35. 18. Reagent 6 is available from Aldrich.