Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones

Russian Chemical Bulletin

Volumn 56, Issue 9, 2007, Pages 1821-1827

  Layeva, A A ^a   Nosova, E V ^a   Lipunova, G N ^a   Trashakhova, T V ^a   Charushin, V N ^b  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

2,4 difluorobenzonitrile; 2 amino 6 fluorobenzonitrile; 6 fluoroanthranilamide; 6 fluoroanthranilic acid; Cyclocondensation; Fluoro containing quinazolin 4 ones; Quinazoline 2,4 dione; Schiff bases

Indexed keywords

EID: 41049108022     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-007-0283-x     Document Type: Article

References (38)

1. S. A. Rocco, J. E. Barbarini, and R. Rittner, Synthesis, 2004, 3, 429.
2. F. Ciardiello, Drugs, 2000, 60, 25.
3. G. W. Rewcastle, W. A. Denny, A. J. Bridges, H. Zhou, D. R. Cody, A. McMichael, and D. W. Fry, J. Med. Chem., 1995, 38, 3482.
4. A. J. Bridges, H. Zhou, D. R. Cody, G. W. Rewcastle, A. McMichael, D. W. Fry, and W. A. Denny, J. Med. Chem., 1996, 39, 267.
5. G. W. Rewcastle, D. K. Murray, W. L. Elliot, D. W. Fry, C. T. Howard, J. A. Nelson, B. J. Roberts, P. W. Vincent, H. D. H. Showalter, R. T. Winters, and W. A. Denny, J. Med. Chem., 1998, 41, 742.
6. W. Szczepankiewicz, J. Suwiski, and R. Bujok, Tetrahedron, 2000, 56, 9343.
7. H. Yang, S. K. Kim, M. Kim, P. A. Reche, T. J. Morehead, I. K. Damon, R. M. Welsh, and E. L. Reinherz, J. Clin. Invest., 2005, 115(2), 379.
8. G. Pentassuglia, B. Bertani, D. Donati, and A. Ursini, J. Heterocycl. Chem., 1996, 33, 1163.
9. C. Parkanyi, H. L. Yuan, B. H. E. Stromberg, and A. Evenzahav, J. Heterocycl. Chem., 1992, 29, 749.
10. RST Int. Appl. WO 99 812 (2003), Chem. Abstrs, 2004, 140, 16739f.
11. G. G. Furin, Ftorsoderzhashchie geterotsiklicheskie soedineniya: sintez i primenenie [Fluoro-Containing Heterocyclic Compounds: Synthesis and Applications], Nauka, Novosibirsk, 2001, 241 pp. (in Russian).
12. V. G. Granik, Osnovy meditsinskoi khimii [Fundamentals of Medicinal Chemistry], Vuzovskaya Kniga, Moscow, 2001, 141 pp. (in Russian).
13. V. S. Mokrushin and G. A. Vavilov, Osnovy khimii i tekhnologii bioorganicheskikh i sinteticheskikh lekarstvennykh veshchestv [Fundamentals of the Chemistry and Technology of Bioorganic and Synthetic Drugs], Ekaterinburg, GOU VPO UGTU-UPI, 2004, 356 pp. (in Russian).
14. L. L. Shen, Quinolone Antibacterial Agents, American Society for Microbiology, Washington, 1993, 176 pp.
15. P. Ball, in The Quinolones, Ed. T. V. Andriole, Academic Press, San Francisco, 1998, 210 pp.
16. RST Int. Appl. WO 99 818 (2003), Chem. Abstrs, 2004, 140, 16739f.
17. RST Int. Appl. WO 47 278 (2005), Chem. Abstrs, 2005, 143, 7722s.
18. W. M. Welch, F. E. Ewing, J. Huang, F. S. Menniti, M. J. Pagnozzi, K. Kelly, P. A. Seymour, V. Guanowsky, S. Guhan, M. R. Guinn, D. Critchett, J. Lazzaro, A. H. Ganong, K. M. DeVries, T. L. Staigers, and B. L. Chenard, Bioorg. Med. Chem. Lett., 2001, 11, 177.
19. Drug Data Report, 1999, 21, 271; 311.
20. Drug Data Report, 1998, 20, 211.
21. D. J. Connoly, D. Cusack, T. P. O'Sullivan, and P. J. Cuiry, Tetrahedron, 2005, 61, 1153.
22. Drug Data Report, 1999, 21, 271; 293.
23. Zayavka RF [RF Application] 116 911/04 (2004), RU BIPM, No. 31b, 10.11.2005 (in Russian).
24. R. J. Abdel-Jalil, H. M. Aldoqum, M. T. Ayoub, and W. Voelter, Heterocycles, 2005, 65(9), 2061.
25. RST Int. Appl. WO 99 778 (2004), Chem. Abstrs, 2004, 141, 410947g.
26. T. Undheim and T. Benneche, in Comprehensive Heterocyclic Chemistry II, Eds A. R. Katritsky, C. W. Rees, and E. V. Scriven, vol. 6, Pergamon Press, Oxford, 1996, pp. 93-231.
27. D. J. Connoly, D. Cusack, T. P. O'Sullivan, and P. S. Guiry, Tetrahedron, 2005, 61, 10153.
28. J. B. Jiang, D. P. Hesson, B. A. Dusak, D. L. Dexter, G. L. Kang, and E. Hamel, J. Med. Chem., 1990, 33, 1721.
29. D. S. Yoon, Y. Han, T. M. Stark, J. C. Haber, B. T. Gregg, and S. B. Stankovich, Org. Lett., 2004, 6, 4775.
30. C. Parkanyi, H. L. Yuan, B. H. E. Stromberg, and A. Evenzahav, J. Heterocycl. Chem., 1992, 29, 749.
31. G. A. Roth and J. J. Tai, J. Heterocycl. Chem., 1996, 33, 2051.
32. A. A. Layeva, E. V. Nosova, G. N. Lipunova, T. V. Trashakhova, and V. N. Charushin, J. Fluorine Chem., 2007, 128, 748.
33. G. R. Dave, G. S. Mewada, and G. C. Amin, J. Indian Chem. Soc., 1960, 38, 295.
34. S. B. Mhaske and N. P. Argade, J. Org. Chem., 2004, 69, 4563.
35. P. S. Reddy, P. P. Reddy, and T. Vasantha, Heterocycles, 2003, 60, 183.
36. R. J. Abdel-Jalil, W. Voelter, and M. Saeed, Tetrahedron Lett., 2004, 45, 3475.
37. E. C. Taylor and R. V. Ravindranathan, J. Org. Chem., 1966, 27, 2622.
38. Yu. M. Volovenko, A. G. Nemazanyi, I. G. Ryabokon', and F. S. Babichev, Ukr. Khim. Zh., 1988, 54, 295 (in Russian).