Structurally diverse 2,6-disubstituted quinoline derivatives by solid-phase synthesis

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2757-2760

  Ruhland, T ^a   Kunzer H ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 3242702692     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00443-1     Document Type: Article

References (20)

1. (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233.
2. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
3. Jung, G.; Beck-Sickinger, A. G. Angew. Chem. 1992, 104, 375; Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
4. Jung, G.; Beck-Sickinger, A. G. Angew. Chem. 1992, 104, 375; Angew. Chem., Int. Ed. Engl. 1992, 31, 367.
5. (a) Leznoff, C. C. Acc. Chem. Res. 1978, 11, 327.
6. (b) Hodge, P. In Syntheses And Separations Using Functional Polymers; Sherrington, D. C. and Hodge, P., Eds.; J. Wiley & Sons, Inc.: New York, 1988; Chapter 2.
7. For most recent developments, see: (a) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
8. (b) Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. ibid. 1995, 117, 5381.
9. (c) Baldwin, J. J.; Burbaum, J. J.; Henderson, I.; Ohlmeyer, M. H. J. ibid. 1995, 117, 5588.
10. (d) Murphy, M. M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. ibid. 1995, 117, 7029.
11. (e) Beebe, X.; Chiappari, C. L.; Olmstead, M. M.; Kurth, M. J.; Schore, N. E. J. Org. Chem. 1995, 60, 4204.
12. For some recent work on pharmacologically interesting quinoline derivatives, consult: (a) Chen, S.-F.; Papp, L. M.; Ardecky, R. J.; Rao, G. V.; Hesson, D. P.; Forbes, M.; Dexter, D. L. Biochem. Pharmacol. 1990, 40, 709.
13. (b) Meanwell, N. A.; Roth, H. R.; Smith, E. C. R.; Wedding, D. L.; Wright, J. J. K.; Fleming, J. S.; Gillespie, E. J. Med. Chem. 1991, 34, 2906.
14. (c) Dow, R. L.; Bechle, B. M.; Chou, T. T.; Goddard, C.; Larson, E. R. Bioorg. & Med. Chem. Lett. 1995, 5, 1007.
15. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37.
16. Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25, 839.
17. Balicki, R.; Kaczmarek, L.; Malinowski, M. Synth. Commun. 1989, 19, 897.
18. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171.
19. Purchased from Rapp Polymere GmbH, Ernst Simon Str. 9, D-72072 Tübingen, Germany.
20. 2) δ 200.1, 173.4, 163.9, 142.8, 140.1, 136.8, 134.0, 129.0, 128.5, 127.9, 114.0, 113.5, 68.7, 66.4, 60.6, 46.9, 34.1, 28.7, 21.8, 14.4. 4: mp 81-82°C (ethyl acetate/hexane). 5: mp 89-90°C (ethyl acetate/hexane). 12aα: mp 147-148°C (dichloromethane/-hexane). 12aβ: mp 141-142°C (acetone/hexane). 12bβ: mp 158-159°C (acetone/hexane). 12cβ: mp 147-148°C (acetone/hexane). 12dβ: mp 116-117°C (acetone/hexane). 12eβ: mp 184-185°C (acetone/hexane). 12fβ: mp 138-139°C (dichloromethane/hexane). 12aγ: mp 125-126°C (acetone/hexane). 12bγ: mp 145-146°C (acetone/hexane). 12cγ: mp 121-122°C (acetone/hexane). 12dγ: mp 132-134°C (acetone/hexane). 12eγ: mp 196-197°C (acetone/hexane). 12fγ: mp 169-170°C (dichloromethane/hexane).