Synthesis of novel fluorinated 4H-benzo[h]chromen-4-one and 4H-pyrano[3,2-h]quinolin-4-one derivatives

Tetrahedron Letters

Volumn 49, Issue 4, 2008, Pages 589-593

  Médebielle, Maurice ^a   Keirouz, Robert ^a   Okada, Etsuji ^b   Shibata, Dai ^b   Dolbier Jr , William R ^c  

^a UNIVERSITÉ LYON 1   (France)

^b KOBE UNIVERSITY   (Japan)

^c University of Florida ^*  (United States)

Author keywords

Electron transfer; Flavone; Fluorine; SNAr; Tetrakis(dimethylamino)ethylene

Indexed keywords

4H BENZO[H]CHROMEN 4 ONE DERIVATIVE; 4H PYRANO[3,2 H]QUINOLINE 4 ONE DERIVATIVE; ACETIC ACID DERIVATIVE; ALDEHYDE; ETHYLENE DERIVATIVE; KETONE DERIVATIVE; N,N DIMETHYLAMINO BIS CHLORODIFLUOROACETYL; TETRAKIS(DIMETHYLAMINO)ETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; FLUORINATION; ONE POT SYNTHESIS;

EID: 37649005538     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.146     Document Type: Article

References (39)

1. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer, Berlin
2. Burger K., Wucherpfennig U., and Brunner E. Adv. Heterocycl. Chem. 60 (1994) 1
3. Bergstrom D.E., and Swartling D.J. Fluorine Substituted Analogues of Nucleic Acid Components. In: Liebman J.F., Greenberg A., and Dolbier Jr. W.R. (Eds). Fluorine-Containing Molecules, Structure, Reactivity, Synthesis and Applications (1988), VCH, New York 259-308
4. Kirsch P. Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim
5. Menichincheri M., Ballinari D., Bargiotti A., Bonommini L., Ceccarelli W., D'Alessio R., Fretta A., Moll J., Polucci P., Soncini C., Tibolla M., Trosset J.-Y., and Vanotti E. J. Med. Chem. 47 (2004) 6466
6. Bauvois B., Puiffe M.-L., Bongui J.-B., Paillat S., Monneret C., and Dauzonne D. J. Med. Chem. 46 (2003) 3900
7. Elangovan V., Sekar N., and Govindasamy S. Cancer Lett. 87 (1994) 107
8. Yu D., Morris-Natschke S.L., and Lee K.-H. Med. Res. Rev. 27 (2007) 108
9. Kashiwada K., Aoshima A., Ikeshiro Y., Chen Y.-P., Furukawa H., Itoigawa M., Fujioka T., Mihashi K., Cosentino L.M., Morris-Natschke S.L., and Lee K.-H. Bioorg. Med. Chem. 13 (2005) 443
10. Yu D., Chen C.-H., Brossi A., and Lee K.-H. J. Med. Chem. 47 (2004) 4072
11. Tillekeratne L.M.V., Sherette A., Grossmann P., Hupe L., Hupe D., and Hudson R.A. Bioorg. Med. Chem. Lett. 11 (2001) 2763
12. Hou Y., Higashiya S., and Fuchigami T. J. Org. Chem. 64 (1999) 3346
13. Dawood K.M., Ishii H., and Fuchigami T. J. Org. Chem. 66 (2001) 7030
14. Andrès D.F., Dietrich U., Laurent E.G., and Marquet B. Tetrahedron 53 (1997) 647
15. Wang C.-L., Li H.-Q., Meng W.-D., and Qing F.-L. Bioorg. Med. Chem. Lett. 15 (2005) 4456
16. Hojo M., Masuda R., Okada E., and Miya H. Synthesis (1989) 870
17. Hojo M., Masuda R., and Okada E. Tetrahedron Lett. 28 (1987) 6199
18. Okada E., Tsukushi N., Otsuki Y., Nishiyama S., and Fukuda T. Synlett (1999) 126
19. Okada E., Tsukushi N., and Shimomura N. Synthesis (2000) 237
20. Okada E., and Tsukushi N. Synlett (1999) 210
21. Okada E., Otsuki Y., Shinohara M., Médebielle M., Shimizu Y., and Takeuchi H. Tetrahedron Lett. 44 (2003) 741
22. 3I by TDAE:. Pooput Jr. C., Dolbier W.R., and Médebielle M. J. Org. Chem. 71 (2006) 3564
23. Médebielle M., Kato K., and Dolbier Jr. W.R. Tetrahedron Lett. 44 (2003) 7871
24. Takechi N., Ait-Mohand S., Médebielle M., and Dolbier Jr. W.R. Org. Lett. 4 (2002) 4671
25. Médebielle M., Kato K., and Dolbier Jr. W.R. Synlett (2002) 1541
26. Médebielle M., Keirouz R., Okada E., and Ashida T. Synlett (2001) 821
27. Billard T., Langlois B.R., and Médebielle M. Tetrahedron Lett. 42 (2001) 3463
28. Ait-Mohand S., Takechi N., Médebielle M., and Dolbier Jr. W.R. Org. Lett. 3 (2001) 4271
29. Burkholder C., Dolbier Jr. W.R., Médebielle M., and Ndedi A. Tetrahedron Lett. 39 (1998) 8853
30. Burkholder C., Dolbier Jr. W.R., and Médebielle M. J. Org. Chem. 63 (1998) 5385
31. We have also demonstrated that the TDAE reagent can be used with non-fluorinated substrates for the synthesis of potential anticancer agents:. Giuglio-Tonolo G., Terme T., Médebielle M., and Vanelle P. Tetrahedron Lett. 44 (2003) 6433
32. Giuglio-Tonolo G., Terme T., Médebielle M., and Vanelle P. Tetrahedron Lett. 45 (2004) 5121
33. Médebielle M., Hohn S., Okada E., Myoken H., and Shibata D. Tetrahedron Lett. 46 (2005) 7817
34. Cardenas M., Marder M., Blank V.C., and Roguin L.P. Bioorg. Med. Chem. 14 (2006) 2966
35. Springsteel M.F., Galietta L.J.V., Ma T., By K., Berger G.O., Yang H., Dicus C.W., Choung W., Quan C., Shelat A.A., Guy R.K., Verkman A.S., Kurth M.J., and Nantz M.H. Bioorg. Med. Chem. 11 (2003) 4113
36. Moro S., Rhee M.V., Sanders L.H., and Jacobson K.A. J. Med. Chem. 41 (1998) 46
37. Karton Y., Jiang J.-L., Ji X.-D., Melman N., Olah M.E., Stiles G.L., and Jacobson K.A. J. Med. Chem. 39 (1996) 2293
38. Hsiao G., Chang C.-Y., Shen M.-Y., Chou D.-S., Tzeng S.-W., Chen T.-F., and Sheu J.-R. J. Agric. Food. Chem. 53 (2005) 5179
39. 4: C, 70.89; H, 3.61. Found 71.20; H, 3.82.