Solid-phase synthesis of pyrazolopyridines from polymer-bound alkyne and azomethine imines

Journal of Combinatorial Chemistry

Volumn 8, Issue 3, 2006, Pages 344-349

  Harju, Kirsi ^a   Kylänlahti, Irene ^a   Paananen, Timo ^a   Polamo, Mika ^a   Nielsen, John ^b   Yli Kauhaluoma, Jari ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZO COMPOUND; AZOMETHANE; IMINE; METHANOL; POLYMER; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; PHARMACEUTICS; SYNTHESIS;

ALKYNES; AZO COMPOUNDS; IMINES; METHANOL; MODELS, CHEMICAL; POLYMERS; PYRAZOLES; PYRIDINES; TECHNOLOGY, PHARMACEUTICAL;

EID: 33744470624     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050138j     Document Type: Article

References (33)

1. Bettinetti, L.; Schlotter, K.; Hübner, H.; Gmeiner, P. J. Med. Chem. 2002, 45, 4594-4597.
2. Löber, S.; Hübner, H.; Utz, W.; Gmeiner, P. J. Med. Chem. 2001, 44, 2691-2694.
3. Kuroda, S.; Akahane, A.; Itani, H.; Nishimura, S.; Durkin, K.; Tenda, Y.; Sakane, K. Bioorg. Med. Chem. 2000, 8, 55-64
4. Johns, B. A.; Gudmundsson, K. S.; Turner, E. M.; Allen, S. H.; Samano, V. A.; Ray, J. A.; Freeman, G. A.; Boyd, F. L.; Sexton, C. J.; Selleseth, D. W.; Creech, K. L.; Moniri, K. R. Bioorg. Med. Chem. 2005, 13, 2397-2411.
5. Irikura, T.; Nishino, K.; Suzue, S.; Ikeda, T. Eur. Pat. Appl. (Kyorin Pharmaceutical Co., Ltd., Japan). EP0118916, Sept. 19, 1984.
6. Harju, K.; Yli-Kauhaluoma, J. Mol. Diversity 2005, 9, 187-207.
7. (a) Moore, M.; Norris, P. Tetrahedron Lett. 1998, 39, 7027-7030.
8. (b) Tørnoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
9. (a) Park, K.-H.; Kurth, M. J. J. Org. Chem. 1999, 64, 9297-9300.
10. (b) Huang, X.; Xu, W.-M. Org. Lett. 2003, 5, 4649-4652.
11. (c) Makaritis, A.; Georgiadis, D.; Dive, V.; Yiotakis, A. Chem-Eur. J. 2003, 9, 2079-2094.
12. (d) Shang, Y.-J.; Wang, Y.-G. Tetrahedron Lett. 2002, 43, 2247-2249.
13. Fuchi, N.; Doi, T.; Takahashi, T. Chem. Lett. 2005, 34, 438-439.
14. Washizuka, K.-I.; Nagai, K.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 2000, 41, 691-695.
15. Donohue, A. C.; Pallich, S.; McCarthy, T. D. J. Chem. Soc., Perkin Trans, 1 2001, 2817-2822.
16. Huisgen, R.; Grashey, R.; Krischke, R. Tetrahedron Lett. 1962, 387-391.
17. Gösl, R.; Meuwsen, A. Org. Synth. Coll. Vol. V 1973, 43-45.
18. Corbett, J. W.; Graciani, N. R.; Mousa, S. A.; DeGrado, W. F. Bioorg. Med. Chem. Lett. 1997, 7, 1371-1376.
19. Bhalay, G.; Blaney, P.; Palmer, V. H.; Baxter, A. D. Tetrahedron Lett. 1997, 38, 8375-8378.
20. (a) Krischke, R.; Grashey, R.; Huisgen, R. Liebigs Ann. Chem. 1977, 506-527.
21. (b) Anderson, P. L.; Hasak, J. P.; Kahle, A. D.; Paolella, N. A.; Shapiro, M. J. J. Heterocycl. Chem. 1981, 18, 1149-1152.
22. Tamura, Y.; Sumida, Y.; Miki, Y.; Ikeda, M. J. Chem. Soc., Perkin Trans, 1 1975, 406-409.
23. (a) Tamura, Y.; Miki, Y.; Ikeda, M. J. Heterocycl. Chem. 1975, 12, 119-122.
24. (b) Sundberg, R. J.; Ellis, J. E. J. Heterocycl. Chem. 1982, 19, 573-576.
25. For representative examples of the yields of pyrazolopyridines, see refs 2, 12, and 16a. See also (a) Boekelheide, V.; Fedoruk, N. A. J. Org. Chem. 1968, 33, 2062-2064.
26. (b) Bettinetti, L.; Löber, S.; Hübner, H.; Gmeiner, P. J. Comb. Chem. 2005, 7, 309-316.
27. Potts, K. T.; Singh, U. P.; Bhattacharyya, J. J. Org. Chem. 1968, 33, 3766-3770.
28. Kohda, K.; Noda, Y.; Aoyama, S.; Umeda, M.; Sumino, T.; Kaiya, T.; Maruyama, W.; Naoi, M. Chem. Res. Toxicol. 1998, 11, 1249-1253.
29. Higashino, T.; Suzuki, Y.; Sasahara, T.; Saito, T.; Mochizuki, D. Eur. Pat. Appl (Toyo Jozo Co., Ltd., Japan) EP0483836, May 6, 1992.
30. Tamura, Y.; Kim, J.-H.; Miki, Y.; Hayashi, H.; Ikeda, M. J. Heterocycl. Chem. 1975, 12, 481-483.
31. Kakehi, A.; Ito, S.; Uchiyama, K.; Konno, Y.; Kondo, K. J. Org. Chem. 1977, 42, 443-448.
32. Miki, Y.; Konishi, M.; Nishikubo, N.; Yoshimaru, T.; Takemura, S. Heterocycles 1983, 20, 201-203.
33. Miki, Y.; Nakamura, N.; Hachiken, H.; Takemura, S. J. Heterocycl. Chem. 1989, 26, 1739-1745.