Synthesis of thiazolo- and 7,8-dihydrothiazolo[4,5-e]benzoisoxazoles

Journal of Combinatorial Chemistry

Volumn 11, Issue 2, 2009, Pages 228-238

  El Badri, M H ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ISOXAZOLE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HALOGENATION; SYNTHESIS;

BENZENE DERIVATIVES; CYCLIZATION; HALOGENATION; ISOXAZOLES; MOLECULAR STRUCTURE; THIAZOLES;

EID: 64949128916     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc800141s     Document Type: Article

References (41)

1. Ji, Z.; Ahmed, A. A.; Albert, D. H.; Bouska, J. J.; Bousquet, P. F.; Cunha, G. A.; Diaz, G.; Glaser, K. B.; Guo, J.; Harris, C. M.; Li, J.; Marcotte, P. A.; Moskey, M. D.; Oie, T.; Pease, L.; Soni, N. B.; Stewart, K. D.; Davidsen, S. K.; Michaelides, M. R. J. Med Chem. 2008, 51, 1231-1241.
2. Thon, V.; Harle, P.; Scholmerich, J.; Kuklinek, P.; Lokaj, J.; Straub, R. H. Allergy (Oxford, U. K.) 2007, 62, 1320-1325.
3. Cullen, M. D.; Deng, B.-L.; Hartman, T. L.; Watson, K. M.; Buckheit, R. W., Jr.; Pannecouque, C.; De Clercq, E.; Cushman, M. J. Med. Chem. 2007, 50, 4854-4867.
4. Barcelo, M.; Ravina, E.; Masaguer, C. F.; Dominguez, E.; Areias, F. M.; Brea, J.; Loza, M. I. Bioorg. Med. Chem. Lett. 2007, 17, 4873-4877.
5. Severance, D. L.; Gardiner, E. M. M.; Noble, S. A.; Lou, B.; Borchardt, A. J.; Kahraman, M.; Roppe, J. R.; Siegel, D. L.; Scranton, S. A. Intl. Patent WO 2006116355 A1, 2006.
6. Donohue, B. A.; Michelotti, E. L.; Reader, J. C.; Reader, V.; Stirling, M.; Tice, C. M. J. Comb. Chem. 2002, 4, 23-32.
7. Forood, B. Intl. Patent WO 2000045635 A1, 2000.
8. Kijjoa, A.; Wattanadilok, R.; Campos, N.; Nascimento, M. S. J.; Pinto, M.; Herz, W. Marine Drugs 2007, 5, 6-22.
9. Kitagawa, H.; Ozawa, T.; Takahata, S.; Iida, M. Bioorg. Med. Chem. Lett. 2007, 17, 4982-4986.
10. Bacskai, B. J.; Hickey, G. A.; Skoch, .T.; Kajdasz, S. T.; Wang, Y.; Huang, G.-F.; Mathis, C. A.; Klunk, W. E.; Hyman, B. T. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 12462-12467.
11. Rao, V. S.; Rao, S. S. P.; Reddy, A. P.; Veeranagaiah, V. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32B, 322-327.
12. Landquist, J. K. J. Chem. Soc., Sect. C: Org. 1967, 21, 2212-2220.
13. Cullen, E.; Becker, R.; Freter, K.; LeClerq, T.; Possanza, G.; Wong, H. C. J. Med. Chem. 1992, 35, 350-361.
14. Rao, E. B.; Kumari, S. S.; Rao, K. M. Indian J. Chem., Sect. B; Org. Chem. Incl. Med. Chem. 1987, 26B, 366-367.
15. (a) Takikawa, H.; Hikita, K.; Suzuki, K. Synlett 2007, 2252-2256.
16. (b) Matsuura, T.; Bode, J. W.; Hachisu, Y.; Suzuki, K. Synlett 2003, 1746-1748.
17. (c) Bode, J. W.; Suzuki, K. Tetrahedron Lett. 2003, 44, 3559-3563.
18. (d) Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Tetrahedron Lett. 2003, 44, 3555-3558.
19. (e) Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Org. Lett. 2003, 5, 391-394.
20. Liu, K.-C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916-3918.
21. (a) Attempts to prepare 5,6-dihydro-4H-cyclopenta[d]isoxazol-4-one employing cyclopentane-1,3-dione failed. .
22. (b) There are numerous literature examples of this cyclocondensation reaction employing various 1,3-diones; for representative examples, see refs 17c-e.
23. (c) Matsuura, T.; Bode, J. W.; Hachisu, Y.; Suzuki, K. Synlett 2003, 1746-1748.
24. (d) Umesha, K. B.; Kumar, K.; Rai, Ajay; Lokanatha., K. M. Synth. Commun. 2002, 32, 1841-1846.
25. (e) Giannella, M.; Gualtieri, F.; Pigini, M. Farmaco Ed. Sci. 1967, 22, 333-341.
26. (a) Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492-3494.
27. (b) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432-8433.
28. Clausen, R. P.; Moltzen, E. K.; Perregaard, J.; Lenz, S. M.; Sanchez, C.; Falch, E.; Frolund, B.; Bolvig, T.; Sarup, A.; Larsson, O. M.; Schousboe, A.; Krogsgaard-Larsen, P. Bioore. Med. Chem. 2005, 13, 895-908.
29. Falch, E.; Perregaard, J.; Frolund, B.; Sokilde, B.; Buur, A.; Hansen, L. M.; Frydenvang, K.; Brehm., L.; Bolvig, T.; Larsson, O. M.; Sanchez, C.; White, H. S.; Schousboe, A.; Krogsgaard-Larsen, P. J. Med. Chem. 1999, 42, 5402-5414.
30. Shutske, G. M. J. Heterocycl. Chem. 1990, 27, 1617-1621.
31. Lakhvich, F. A.; Petrusevich, I. I.; Buravskaya, T. N. Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk 1989, 64-68.
32. Chiarino, D.; Grancini, G.; Frigeni, V.; Biasini, I.; Carenzi, A. J. Med. Chem. 1991, 34, 600-605.
33. For examples of heterocycle-thiazole formation, see: (a) Lu, J.-Y.; Arndt, H.-D. J. Org. Chem. 2007, 72, 4205-4212.
34. (b) Mashraqui, S. H.; Mistry, H.; Sundaram, S. J. Heterocycl. Chem. 2006, 43, 917-923.
35. (c) Clough, J. M.; Dube, H.; Martin, B. J.; Pattenden, G.; Reddy, K. S.; Waldron, I. R. Org. Biomol. Chem. 2006, 4, 2906-2911.
36. (d) Hearn, B. R.; Zhang, D.; Li, Y.; Myles, D. C. Org. Lett. 2006, 8, 3057-3059.
37. (a) Loska, R.; Maükosza, M. J. Org. Chem. 2007, 72, 1354-1365.
38. (b) Sissouma, D.; Maingot, L.; Collet, S.; Guingant, A. J. Org. Chem. 2006, 71, 8384-8389.
39. Goeblyoes, A.; Santiago, S. N.; Pietra, D.; Mulder-Krieger, T.; von Frijtag Drabbe Kuenzel, J.; Brussee, J.; IJzerman, A. P. Bioorg. Med. Chem. 2005, 13, 2079-2087.
40. Fravolini, A.; Grandolini, G.; Martani, A. Gazz. Chim. Ital. 1973, 103, 755-69.
41. Curphey, T. J. J. Org. Chem. 2002, 67, 6461-6473.