High throughput synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b] thiazole derivatives

Tetrahedron Letters

Volumn 52, Issue 6, 2011, Pages 696-698

  Li, Yangmei ^a   Giulianotti, Marc ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,6 DIHYDROIMIDAZO[2,1 B]THIAZOLE DERIVATIVE; DIAMINE; ENAMINE; HALOKETONE; IMIDAZO[2,1 B]THIAZOLE DERIVATIVE; RESIN; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; SOLID PHASE SYNTHESIS; SUBSTITUTION REACTION;

EID: 79251600930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.006     Document Type: Article

References (23)

1. V. Krchnák, and M.W. Holladay Chem. Rev. 102 2002 61
2. A. Nefzi, J.M. Ostresh, and R.A. Houghten Chem. Rev. 97 1997 449
3. B.K. Cassels, I. Bermúdez, F. Dajas, J.A. Abin-Carriquiry, and W. Susan Drug Discov. Today 10 2005 1657
4. T.H. Marsilje, J.B. Roses, E.F. Calderwood, S.G. Stroud, N.E. Forsyth, C. Blackburn, D.L. Yowe, W.Y. Miao, S.V. Drabic, M.D. Bohane, J.S. Daniels, P. Li, L.J. Wu, M.A. Patane, and C.F. Claiborne Bioorg. Med. Chem. Lett. 14 2004 3721
5. L.B. Townsend Chem. Rev. 67 1967 533
6. R. Silvestri, M. Artico, G. La Regina, A. Di Pasquali, G. De Martino, F.D. D'Auria, L. Nencioni, and A.T. Palamara J. Med. Chem. 47 2004 3926
7. P.J. Sanfilippo, M.C. Jetter, R. Cordova, R.A. Noe, E. Chourmouzis, C.Y. Lau, and E. Wang J. Med. Chem. 38 1995 1057
8. J.E. van Muijlwijk-Koezen, H. Timmerman, R.C. Vollinga, J. Frijtag von Drabbe Künzel, M. de Groote, S. Visser, and A.P. Ijzerman J. Med. Chem. 44 2001 749
9. L. De Luca Curr. Med. Chem. 13 2006 1
10. Z. Jin Nat. Prod. Rep. 23 2006 464
11. T. Eicher, and S. Hauptmann The Chemistry of Heterocycles 2nd ed. 2003 WILEY-VCH 173
12. Raeymaekers, A. H. M.; Roevens, L. F. C.; van Laerhoven, W. J. C.; van Wauwe, J. P. F. U.S. Patent, 1996; 5527915.
13. Nishio, K.; Chiyomaru, I.; Anma, K.; Yamamoto, K.; Ohno, H.; Takayanagi, N. U.S. Patent, 1985; 4556669.
14. Yamamoto, I.; Matsunari, K.; Nitta, K.; Shibata, K.; Takayanaqi, N. U.S. Patent, 1990; 4910315.
15. A. Scribner, S. Meitz, M. Fisher, M. Wyvratt, L. Penny, P. Liberatoe, A. Gurnett, C. Brown, J. Mathew, D. Thompson, D. Schmatz, and T. Biftu Bioorg. Med. Chem. Lett. 18 2008 5263
16. C.G. Moertel, T.R. Fleming, J.S. Macdonald, D.G. Haller, J.A. Laurie, C.M. Tangen, J.S. Ungerleider, W.A. Emerson, D.C. Tormey, J.H. Glick, M.H. Veeder, and J.A. Mailliard Ann. Intern. Med. 122 1995 321
17. For method i: S. Debre, N. Lecat-Guillet, F. Pillon, and Y. Ambroise Bioorg. Med. Chem. Lett. 19 2009 825
18. N. Lecat-Guillet, and Y. Ambroise ChemMedChem 2008 1211
19. R.S. Varma, D. Kumar, and P.J. Liesen J. Chem. Soc. Perk. T. 1. 1998 4093
20. V.M. Dianov, M.K. Zeleev, and L.V. Spirikhin Russ. J. Org. Chem. 41 2005 153
21. For method ii: L. Li, L. Chang, S. Pellet-Rostaing, F. Liger, M. Lemaire, R. Buchet, and Y. Wu Bioorg. Med. Chem. 17 2009 7290
22. V. Birman, and X. Li Org. Lett. 7 2006 1351
23. 3) δ: 2.00 (s, 3H), 2.07 (s, 3H), 2.87 (dd, 1H, J = 9.2, 13.6 Hz), 3.06 (dd, 1H, J = 4.3, 13.6 Hz), 3.97 (dd, 1H, J = 3.9, 12.8 Hz), 4.11 (dd, 1H, J = 9.3, 12.8 Hz), 4.41-4.46 (m, 1H), 7.17 (d, 2H, J = 7.1 Hz), 7.27-7.36 (m, 3H).