Synthesis of a quinolone library from ynones

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6494-6497

  Ward, Timothy R ^a   Turunen, Brandon J ^a   Haack, Torsten ^a   Neuenswander, Benjamin ^a   Shadrick, William ^a   Georg, Gunda I ^b  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRANILIC ACID DERIVATIVE; QUINOLONE DERIVATIVE;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 78149352633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.024     Document Type: Article

References (12)

1. (a) Turunen, B. J.; Georg, G. I. J. Am. Chem. Soc. 2006, 128, 8702;
2. (b) Wang, X.; Turunen, B. J.; Leighty, M. W.; Georg, G. I. Tetrahedron Lett. 2007, 48, 8811;
3. (c) Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708.
4. Kuo, S. C.; Lee, H. Z.; Juang, J. P.; Lin, Y. T.; Wu, T. S.; Chang, J. J.; Lednicer, D.; Paull, K. D.; Lin, C. M.; Hamel, E.; Lee, K. H. J. Med. Chem. 1993, 36, 1146.
5. Li, L.; Wang, H. K.; Kuo, S. C.; Wu, T. S.; Lednicer, D.; Lin, C. M.; Hamel, E.; Lee, K. H. J. Med. Chem. 1994, 37, 1126;
6. For related syntheses see: Chen, B. C.; Huang, X.; Wang, J. Synthesis 1987, 482;
7. Kasahara, A.; Izumi, T.; Watabe, H.; Takahashi, S. Chem. Indust. 1981, 121.
8. Li, L.; Wang, H. K.; Kuo, S. C.; Wu, T. S.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K. H. J. Med. Chem. 1994, 37, 3400.
9. Grohe, K.; Zeiler, H.J.; Metzger, K. (Bayer, A.-G., Fed. Rep. Ger.). Ger. Offen. 1983, DE 3142854 A1 (19830511).
10. Llinas-Brunet, M.; Bailey, M. D.; Ghiro, E.; Gorys, V.; Halmos, T.; Poirier, M.; Rancourt, J.; Goudreau, N. J. Med. Chem. 2004, 47, 6584.
11. Pesci, E. C.; Milbank, J. B.; Pearson, J. P.; McKnight, S.; Kende, A. S.; Greenberg, E. P.; Iglewski, B. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 11229.
12. The standards for compound purity and quality are based on those requested for the National Institutes of Health's Molecular Libraries Small Molecule Repository (http://mlsmr.glpg.com/MLSMR-HomePage/submitcompounds.html). The compound purities were determined by reverse-phase HPLC with peak area (UV) at 214 nm.