New synthetic pathway to diverse 2-substituted quinolines based on a multicomponent reaction: Solution-phase and solid-phase applications

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 768-775

  Demaude, Thierry ^a   Knerr, Laurent ^a,b   Pasau, Patrick ^a  

^a UCB PHARMA   (Belgium)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,5 DIFLUOROPHENYL) 6 METHOXYQUINOLINE; 2 (2,5 DIFLUOROPHENYL) 6 METHYLQUINOLINE; 2 (2,5 DIFLUOROPHENYL) 8 QUINOLINE; 2 (2,5 DIFLUOROPHENYL)QUINOLINE; 2 (2,5 DIFLUOROPHENYL)QUINOLINE 8 CARBOXYLIC ACID METHYL ESTER; 2 (2,6 DICHLOROPHENYL) 4 N BUTOXY 1,2,3,4 TETRAHYDROQUINOLINE; 2 (2,6 DICHLOROPHENYL) 4 PHENYLTHIO 1,2,3,4 TETRAHYDROQUINOLINE; 2 (2,6 DICHLOROPHENYL) 4 TERT BUTOXY 1,2,3,4 TETRAHYDROQUINOLINE; 2 (3 METHOXYPHENYL) 6 METHOXYQUINOLINE; 2 (3 METHOXYPHENYL) 6 METHYLQUINOLINE; 2 (3 METHOXYPHENYL) 8 CHLOROQUINOLINE; 2 (3 METHOXYPHENYL)QUINOLINE; 2 (3 METHOXYPHENYL)QUINOLINE 8 CARBOXYLIC ACID METHYL ESTER; 2 ([3]THIENYL) 6 METHOXYQUINOLINE; 2 ([3]THIENYL) 6 METHYLQUINOLINE; 2 ([3]THIENYL) 8 CHLOROQUINOLINE; 2 ([3]THIENYL)QUINOLINE; 2 ([3]THIENYL)QUINOLINE 8 CARBOXYLIC ACID METHYL ESTER; 2 BENZOFURAN 2 YL 6 METHOXYQUINOLINE; 2 BENZOFURAN 2 YL 6 METHYLQUINOLINE; 2 BENZOFURAN 2 YL 8 CHLOROQUINOLINE; 2 BENZOFURAN 2 YLQUINOLINE; 2 BENZOFURAN 2 YLQUINOLINE 8 CARBOXYLIC ACID METHYL ESTER; 2 PHENYL 6 METHOXYQUINOLINE; 2 PHENYL 6 METHYLQUINOLINE; 2 PHENYL 8 CHLOROQUINOLINE; 2 PHENYLQUINOLINE; 2 PHENYLQUINOLINE 8 CARBOXYLIC ACID METHYL ESTER; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VERY LATE ACTIVATION ANTIGEN 4;

ARTICLE; COMBINATORIAL LIBRARY; DRUG SYNTHESIS; LIQUID; METHODOLOGY; PYROLYSIS; SOLID;

EID: 4944240436     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049937c     Document Type: Article

References (35)

1. Orru, M. V. A.; de Greef, M. Synthesis 2003, 1471-1499 and references therein.
2. Atwell, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1989, 32, 393-401.
3. Selected references: (a) Gauthier, J. Y.; Jones, T.; Champion, E.; Charette, L.; Dehaven, R.; Ford-Hutchinson, A. W.; Hoogsten, K.; Lord, A.; Masson, P.; Piechuta, H.; Pong, S. S.; Springer, J. P.; Therien, M.; Zamboni, R.; Young, R. N. J. Med. Chem. 1990, 33, 2841-2845. (b) Sawyer, J. S.; Thrasher K. J.; Bach, N. J.; Stengel, P. W.; Cockerham, S. L.; Silbaugh, S. A.; Roman, C. R.; Froelich, L. L.; Fleisch, J. H. Bioorg. Med. Chem. Lett. 1996, 6, 249-252. (c) Zwaagstra, M. E.; Timmerman, H.; van de Stolpe, A. C.; de Kanter, F. J.; Tamura, M.; Wada, Y.; Zhang, M.-Q. J. Med. Chem. 1998, 41, 1428-1438. (d) Chambers, R. J.; Antognoli, G. W.; Cheng, J. B.; Kuperman, A. V.; Liston, T. C.; Marfat, A.; Owens, B. S.; Pillar, J. S.; Shirley, J. T.; Watson, J. W. Bioorg. Med. Chem. Lett. 1998, 8, 3577-3582.
4. Selected references: (a) Gauthier, J. Y.; Jones, T.; Champion, E.; Charette, L.; Dehaven, R.; Ford-Hutchinson, A. W.; Hoogsten, K.; Lord, A.; Masson, P.; Piechuta, H.; Pong, S. S.; Springer, J. P.; Therien, M.; Zamboni, R.; Young, R. N. J. Med. Chem. 1990, 33, 2841-2845. (b) Sawyer, J. S.; Thrasher K. J.; Bach, N. J.; Stengel, P. W.; Cockerham, S. L.; Silbaugh, S. A.; Roman, C. R.; Froelich, L. L.; Fleisch, J. H. Bioorg. Med. Chem. Lett. 1996, 6, 249-252. (c) Zwaagstra, M. E.; Timmerman, H.; van de Stolpe, A. C.; de Kanter, F. J.; Tamura, M.; Wada, Y.; Zhang, M.-Q. J. Med. Chem. 1998, 41, 1428-1438. (d) Chambers, R. J.; Antognoli, G. W.; Cheng, J. B.; Kuperman, A. V.; Liston, T. C.; Marfat, A.; Owens, B. S.; Pillar, J. S.; Shirley, J. T.; Watson, J. W. Bioorg. Med. Chem. Lett. 1998, 8, 3577-3582.
5. Selected references: (a) Gauthier, J. Y.; Jones, T.; Champion, E.; Charette, L.; Dehaven, R.; Ford-Hutchinson, A. W.; Hoogsten, K.; Lord, A.; Masson, P.; Piechuta, H.; Pong, S. S.; Springer, J. P.; Therien, M.; Zamboni, R.; Young, R. N. J. Med. Chem. 1990, 33, 2841-2845. (b) Sawyer, J. S.; Thrasher K. J.; Bach, N. J.; Stengel, P. W.; Cockerham, S. L.; Silbaugh, S. A.; Roman, C. R.; Froelich, L. L.; Fleisch, J. H. Bioorg. Med. Chem. Lett. 1996, 6, 249-252. (c) Zwaagstra, M. E.; Timmerman, H.; van de Stolpe, A. C.; de Kanter, F. J.; Tamura, M.; Wada, Y.; Zhang, M.-Q. J. Med. Chem. 1998, 41, 1428-1438. (d) Chambers, R. J.; Antognoli, G. W.; Cheng, J. B.; Kuperman, A. V.; Liston, T. C.; Marfat, A.; Owens, B. S.; Pillar, J. S.; Shirley, J. T.; Watson, J. W. Bioorg. Med. Chem. Lett. 1998, 8, 3577-3582.
6. Selected references: (a) Gauthier, J. Y.; Jones, T.; Champion, E.; Charette, L.; Dehaven, R.; Ford-Hutchinson, A. W.; Hoogsten, K.; Lord, A.; Masson, P.; Piechuta, H.; Pong, S. S.; Springer, J. P.; Therien, M.; Zamboni, R.; Young, R. N. J. Med. Chem. 1990, 33, 2841-2845. (b) Sawyer, J. S.; Thrasher K. J.; Bach, N. J.; Stengel, P. W.; Cockerham, S. L.; Silbaugh, S. A.; Roman, C. R.; Froelich, L. L.; Fleisch, J. H. Bioorg. Med. Chem. Lett. 1996, 6, 249-252. (c) Zwaagstra, M. E.; Timmerman, H.; van de Stolpe, A. C.; de Kanter, F. J.; Tamura, M.; Wada, Y.; Zhang, M.-Q. J. Med. Chem. 1998, 41, 1428-1438. (d) Chambers, R. J.; Antognoli, G. W.; Cheng, J. B.; Kuperman, A. V.; Liston, T. C.; Marfat, A.; Owens, B. S.; Pillar, J. S.; Shirley, J. T.; Watson, J. W. Bioorg. Med. Chem. Lett. 1998, 8, 3577-3582.
7. Munos, M.-H.; Mayrargue, J.; Fournet, A.; Gantier, J.-C.; Hocquemiller, R.; Moskowitz, H. Chem. Pharm. Bull. 1994, 9, 1914-1916.
8. Zouhiri, F.; Desmaele, D.; d'Angelo, J.; Ourevitch, M.; Mouscadet, J.-F.; Leh, H.; Le Bret, M. Tetrahedron Lett. 2001, 46, 8189-8192.
9. Selected references: (a) Buckley, G. M.; Cooper, N.; Dyke, H. J.; Galleway, F. P.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Maxey, R.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Picken, C. L.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1613-1615. (b) Billah, M.; Buckley, G. M.; Cooper, N.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Oxford, J.; Peake, J. C.; Picken, C. L.; Piwinski, J. J.; Naylor, R.; Sabin, V.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1617-1619. (c) Billah, M.; Cooper, N.; Cuss, F.; Davenport, R. J.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Hannah, D. R.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Piwinski, J. J.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1621-1623.
10. Selected references: (a) Buckley, G. M.; Cooper, N.; Dyke, H. J.; Galleway, F. P.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Maxey, R.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Picken, C. L.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1613-1615. (b) Billah, M.; Buckley, G. M.; Cooper, N.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Oxford, J.; Peake, J. C.; Picken, C. L.; Piwinski, J. J.; Naylor, R.; Sabin, V.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1617-1619. (c) Billah, M.; Cooper, N.; Cuss, F.; Davenport, R. J.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Hannah, D. R.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Piwinski, J. J.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1621-1623.
11. Selected references: (a) Buckley, G. M.; Cooper, N.; Dyke, H. J.; Galleway, F. P.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Maxey, R.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Picken, C. L.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1613-1615. (b) Billah, M.; Buckley, G. M.; Cooper, N.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Oxford, J.; Peake, J. C.; Picken, C. L.; Piwinski, J. J.; Naylor, R.; Sabin, V.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1617-1619. (c) Billah, M.; Cooper, N.; Cuss, F.; Davenport, R. J.; Dyke, H. J.; Egan, R.; Ganguly, A.; Gowers, L.; Hannah, D. R.; Haughan, A. F.; Kendall, H. J.; Lowe, C.; Minnicozzi, M.; Montana, J. G.; Naylor, R.; Oxford, J.; Peake, J. C.; Piwinski, J. J.; Runcie, K. A.; Sabin, V.; Sharpe, A.; Shih, N. Y.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2002, 12, 1621-1623.
12. For some selected recent references, see: (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255-257. (b) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. (c) Söderberg, B. C. G.; Shriver, J. A.; Cooper, S. H.; Shrout, T. L.; Helton, E. S.; Austin, L. R.; Odens, H. H.; Hearn, B. R.; Jones, P. C.; Kouadio, T. N.; Ngi, T. H.; Baswell, R.; Caprara, H. J.; Meritt, M. D.; Mai, T. T. Tetrahedron 2003, 59, 8775-8791. (d) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610-1614. (e) McNaughton, B. R.; Miller, B. L. Org. Lett. In press.
13. For some selected recent references, see: (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255-257. (b) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. (c) Söderberg, B. C. G.; Shriver, J. A.; Cooper, S. H.; Shrout, T. L.; Helton, E. S.; Austin, L. R.; Odens, H. H.; Hearn, B. R.; Jones, P. C.; Kouadio, T. N.; Ngi, T. H.; Baswell, R.; Caprara, H. J.; Meritt, M. D.; Mai, T. T. Tetrahedron 2003, 59, 8775-8791. (d) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610-1614. (e) McNaughton, B. R.; Miller, B. L. Org. Lett. In press.
14. For some selected recent references, see: (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255-257. (b) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. (c) Söderberg, B. C. G.; Shriver, J. A.; Cooper, S. H.; Shrout, T. L.; Helton, E. S.; Austin, L. R.; Odens, H. H.; Hearn, B. R.; Jones, P. C.; Kouadio, T. N.; Ngi, T. H.; Baswell, R.; Caprara, H. J.; Meritt, M. D.; Mai, T. T. Tetrahedron 2003, 59, 8775-8791. (d) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610-1614. (e) McNaughton, B. R.; Miller, B. L. Org. Lett. In press.
15. For some selected recent references, see: (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255-257. (b) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. (c) Söderberg, B. C. G.; Shriver, J. A.; Cooper, S. H.; Shrout, T. L.; Helton, E. S.; Austin, L. R.; Odens, H. H.; Hearn, B. R.; Jones, P. C.; Kouadio, T. N.; Ngi, T. H.; Baswell, R.; Caprara, H. J.; Meritt, M. D.; Mai, T. T. Tetrahedron 2003, 59, 8775-8791. (d) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610-1614. (e) McNaughton, B. R.; Miller, B. L. Org. Lett. In press.
16. For some selected recent references, see: (a) Song, S. J.; Cho, S. J.; Park, D. K.; Kwon, T. W.; Jenekhe, S. A. Tetrahedron Lett. 2003, 44, 255-257. (b) Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813-819. (c) Söderberg, B. C. G.; Shriver, J. A.; Cooper, S. H.; Shrout, T. L.; Helton, E. S.; Austin, L. R.; Odens, H. H.; Hearn, B. R.; Jones, P. C.; Kouadio, T. N.; Ngi, T. H.; Baswell, R.; Caprara, H. J.; Meritt, M. D.; Mai, T. T. Tetrahedron 2003, 59, 8775-8791. (d) Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610-1614. (e) McNaughton, B. R.; Miller, B. L. Org. Lett. In press.
17. (a) Ruhland, T.; Künzer, H. Tetrahedron Lett. 1996, 37, 2757-2760.
18. (b) Gopalsamy, A.; Pallai, P. A. Tetrahedron Lett. 1997, 38, 907-910.
19. (c) Hoemann, M. Z.; Melikian-Badalian, A.; Kumaravel, G.; Hauske, J. R. Tetrahedron Lett. 1998, 39, 4749-4752.
20. (d) Patteux, C.; Levacher, V.; Dupas, G. Org. Lett. 2003, 5, 3061-3063.
21. (a) Matsugi M.; Tabusa, F.; Minamikawa, J. Tetrahedron Lett. 2000, 41, 8523-8525.
22. (b) Fakhfakh, M. A.; Franck, X.; Fournet, A.; Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 2001, 42, 3847-3850.
23. (c) Cho, C. S.; Kim, B. T.; Choi, H. J.; Kim, T. J.; Shim, S. C. Ru Tetrahedron 2003, 59, 7997-8002.
24. Katrizky, A. R.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070.
25. Grieco, P.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858.
26. Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1994, 1195-1202.
27. Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Y Synthesis 1995, 801-804.
28. Crousse, B.; Begue, J.; Bonnet-Delpon, D. J. Org. Chem. 2000, 16, 5009-5013.
29. Solladié, G. Synthesis 1981, 185-196.
30. Harrison, C. R.; Hodge, P. J. Chem. Soc., Perkin Trans. 1 1982, 509-511.
31. Kiselyov, A. S.; Smith, L., II; Armstrong, R. W. Tetrahedron 1998, 20, 5089-5096.
32. Commercially available from Novabiochem.
33. 2 in refluxing MeOH, coevaporated several times with toluene, and dried under high vacuum. Each crude was then divided into two portions. The first portions were analyzed by chiral HPLC. The second portions were epimerized using PS-TBD in refluxing MeOH to yield mixtures of enantiomers that were in turn analyzed by chiral HPLC after resin filtration. All the methyl esters thus obtained were found to be homogeneous by LC/MS. For the chiral HPLCs recorded, see the Supporting Information.
34. (a) Lassoie, M. A.; Knerr, L.; Demaude, T.; De Laveleye, F.; Kogej, T.; Routier, S.; Guillaumet, G. 2,6-Quinolinyl and 2,6-Naphthyl Derivatives, Processes for Preparing Them and Their Uses as VLA-4 Inhibitors. PCT Int. Appl. WO03093237 A1; 2003.
35. Christensen, T. A Acta Chem. Scand. B 1979, 33, 763-766.