Solid phase parallel synthesis of highly substituted thiophene derivatives and identification of novel phosphodiesterase-4 (PDE-4) inhibitors

Tetrahedron

Volumn 55, Issue 39, 1999, Pages 11669-11685

  Han, Yongxin ^a   Giroux, André ^a   Lépine, Carole ^a   Laliberté, France ^b   Huang, Zheng ^b   Perrier, Hélène ^a   Bayly, Christopher I ^a   Young, Robert N ^a  

^a Department of Medicinal Chemistry ^*  (Canada)

^b MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; PHOSPHODIESTERASE IV; PHOSPHODIESTERASE IV INHIBITOR; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; DRUG CONFORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0033600885     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00686-9     Document Type: Article

References (62)

1. Giembycz, J. A.; Dent, G. Clin. Exp. Allergy 1992, 22, 337.
2. Torphy T. J.; Undem, B. J. Thorax 1991, 46, 512.
3. For a recent review, see: Norman P. in "PDE-4 inhibitor 1998", Exp. Opin. Ther. Patents 1998, 8, 771- 784.
4. Kumar, A.; Boykin, D. W. Synth. Commun. 1995, 25, 2071 and references cited therein.
5. Perry, M. J.; O'Connell, J.; Walker, C.; Crabbe, T.; Baldock, D. Russell, A.; Lumb, S.; Huang, Z.; Howat, D.; Allen, R.; Merriman, M.; Walls, J.; Daniel, T.; Hughes, B.; Laliberte, F.; Higgs, G. A.; Owens, R. J. Cell Biochem. Biophys. 1998, 29, 113. Assay was carried out according to the instructions provided by Amersham life science Inc..
6. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
7. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
8. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
9. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
10. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
11. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
12. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
13. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
14. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
15. For reviews, see: Lam, K. S.; Lebl, M.; Krchñák, V. Chem. Rev. 1997, 97, 411; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449; Pirrung, M. C. Chem. Rev. 1997, 97, 473; Balkenhohl, F.; van dem Bussch-Hunnefeld.; Lansky, A.; Zechel, C. Angew. Chem. Ed. Engl. 1996, 35, 2288; Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555; Ellman, J. A. Acc. Chem. Res. 1996, 29, 132; Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144; Still, W. C. Acc. Chem. Res. 1996, 29, 155; Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233 and 1358; DeWitt, S. H.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
16. Boger, D. L.; Chai, W. Tetrahedron 1998, 54, 3955 and references cited therein; An, H.; Wang, T.; Mohan, V.; Griffey, R. H.; Cook, P. D. Tetrahedron 1998, 54, 3999; Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Tetrahedron 1998, 54, 4085; Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
17. Boger, D. L.; Chai, W. Tetrahedron 1998, 54, 3955 and references cited therein; An, H.; Wang, T.; Mohan, V.; Griffey, R. H.; Cook, P. D. Tetrahedron 1998, 54, 3999; Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Tetrahedron 1998, 54, 4085; Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
18. Boger, D. L.; Chai, W. Tetrahedron 1998, 54, 3955 and references cited therein; An, H.; Wang, T.; Mohan, V.; Griffey, R. H.; Cook, P. D. Tetrahedron 1998, 54, 3999; Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Tetrahedron 1998, 54, 4085; Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
19. Boger, D. L.; Chai, W. Tetrahedron 1998, 54, 3955 and references cited therein; An, H.; Wang, T.; Mohan, V.; Griffey, R. H.; Cook, P. D. Tetrahedron 1998, 54, 3999; Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Tetrahedron 1998, 54, 4085; Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097.
20. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
21. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
22. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
23. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
24. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
25. Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193; Kaldor, S. W.; Fritz, J. E.; Tang J.; McKinney, E. R. Bioorg. Med. Chem. Lett. 1996, 6, 3041; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874; Booth R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882; Creswell, M. W.; Bolton, G. L.; Hodges, J. C.; Meppen, M. Tetrahedron 1998, 54, 3983; Parlow, J. J.; Flynn, D. L. Tetrahedron 1998, 54, 4013.
26. Suto, M.; Gayo-Fung, L. M.; Palanki, O. S. S.; Sullivan, R. Tetrahedron 1998, 54, 4141; Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357; Gayo M. L.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513; Parlow, J. J. Tetrahedron Lett. 1996, 37, 5257.
27. Suto, M.; Gayo-Fung, L. M.; Palanki, O. S. S.; Sullivan, R. Tetrahedron 1998, 54, 4141; Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357; Gayo M. L.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513; Parlow, J. J. Tetrahedron Lett. 1996, 37, 5257.
28. Suto, M.; Gayo-Fung, L. M.; Palanki, O. S. S.; Sullivan, R. Tetrahedron 1998, 54, 4141; Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357; Gayo M. L.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513; Parlow, J. J. Tetrahedron Lett. 1996, 37, 5257.
29. Suto, M.; Gayo-Fung, L. M.; Palanki, O. S. S.; Sullivan, R. Tetrahedron 1998, 54, 4141; Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357; Gayo M. L.; Suto, M. J. Tetrahedron Lett. 1997, 38, 513; Parlow, J. J. Tetrahedron Lett. 1996, 37, 5257.
30. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
31. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489; Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. USA 1995, 92, 6419.
32. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489; Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. USA 1995, 92, 6419.
33. For reviews, see: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527; Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating T. A. Acc. Chem. Res. 1996, 29, 123.
34. For reviews, see: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527; Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating T. A. Acc. Chem. Res. 1996, 29, 123.
35. For reviews, see: Früchtel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527; Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating T. A. Acc. Chem. Res. 1996, 29, 123.
36. Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096; Zaragoza, F. Tetrahedron Lett. 1996, 37, 6213; Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973; Whitehouse, D. L.; Nelson Jr., K. H.; Savinov, S. N.; Austin, D. A. Tetrahedron Lett. 1997, 38, 7139.
37. Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096; Zaragoza, F. Tetrahedron Lett. 1996, 37, 6213; Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973; Whitehouse, D. L.; Nelson Jr., K. H.; Savinov, S. N.; Austin, D. A. Tetrahedron Lett. 1997, 38, 7139.
38. Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096; Zaragoza, F. Tetrahedron Lett. 1996, 37, 6213; Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973; Whitehouse, D. L.; Nelson Jr., K. H.; Savinov, S. N.; Austin, D. A. Tetrahedron Lett. 1997, 38, 7139.
39. Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096; Zaragoza, F. Tetrahedron Lett. 1996, 37, 6213; Gowravaram, M. R.; Gallop, M. A. Tetrahedron Lett. 1997, 38, 6973; Whitehouse, D. L.; Nelson Jr., K. H.; Savinov, S. N.; Austin, D. A. Tetrahedron Lett. 1997, 38, 7139.
40. The synthesis of furan libraries are in progress.
41. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
42. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
43. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
44. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
45. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
46. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
47. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
48. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
49. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
50. For solid phase Suzuki coupling reaction of boronic acids and boronic esters, see: Friesen, R. W.; Frenette, R. Tetrahedron Lett. 1994, 35, 9177; Ellman, J. A.; Backes, B. J. J. Am. Chem. Soc. 1994, 116, 11171; Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.; Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169; Piettre, S. R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197; For solid phase Negishi coupling reactions with zincates, see: Rottlander, M.; Knochel, P. Synlett 1997, 1084; Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491; For selected example of solid phase Stille coupling reactions with stannanes, see: Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997; Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613; Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
51. Unpublished results using 4-trimethylsilylthiophene-2-boronic acid and 4-trimethylsilylfuran-2-boronic acid as scaffolds for preparing tri-aryl-thiophene and -furan derivatives.
52. The preparation of this boronic acid and its reaction with aryl or alkenyl halides under the Suzuki coupling reaction conditions in solution will be reported elsewhere.
53. 2/AcOH.
54. Carreño, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem. 1995, 60, 5328; Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733.
55. Carreño, M. C.; Ruano, J. L. G.; Sanz, G.; Toledo, M. A.; Urbano, A. J. Org. Chem. 1995, 60, 5328; Mitchell, R. H.; Lai, Y. H.; Williams, R. V. J. Org. Chem. 1979, 44, 4733.
56. Kellogg, R. M.; Schaap, A. P.; Harper, E. T.; Wynberg, H. J. Org. Chem. 1968, 33, 2902.
57. Bis-alkylation of primary amines on solid support or amide formation during cleavage were possible causes for by-product formation.
58. Souness, J. E.; Griffin, M.; Maselen, C.; Ebsworth, K.; Scott, L. C.; Pollock, K.; Palfreyman, M. N.; Karlsson, J. Br. J. Pharmacol. 1996, 118, 649.
59. Over 20 other structurally diverse boronic acids were studied in solution phase synthesis following similar protocols.
60. The Suzuki coupling reaction of solid supported benzyl bromides with boronic acids was first explored by Yves Gareau and Hélène Juteau at Merck Frosst.
61. Lithium borate complex 17 was provided by Denis Deschênes from Merck Frosst.
62. Meyer, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36.