A versatile synthesis of fluorinated uracils in solution and on solid-phase

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1417-1420

  Fustero, Santos ^a   Piera, Julio ^a   Sanz Cervera, Juan F ^a   Catalán, Silvia ^a   De Arellano, Carmen Ramírez ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; FLUORINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; THIOURACIL DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; POLYMERIZATION; SOLID;

HYDROCARBONS, FLUORINATED; ISOCYANATES; ISOTHIOCYANATES; MOLECULAR STRUCTURE; NITRILES; SOLUTIONS; URACIL;

EID: 2442514289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049668z     Document Type: Article

References (28)

1. Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993.
2. Ozaki, S. Med. Res. Rev. 1996, 16, 51-86.
3. As examples, see: (a) Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001. (b) Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001. (c) Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998. (d) Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997. (e) Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
4. As examples, see: (a) Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001. (b) Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001. (c) Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998. (d) Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997. (e) Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
5. As examples, see: (a) Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001. (b) Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001. (c) Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998. (d) Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997. (e) Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
6. As examples, see: (a) Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001. (b) Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001. (c) Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998. (d) Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997. (e) Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
7. As examples, see: (a) Tohyama, Y.; Sanemitsu, Y. Eur. Pat. Appl. EP 1122244 A1, 2001. (b) Theodoridis, G.; Crawford, S. D. (FMC Corporation, USA) US 6277847 B1, 2001. (c) Drewes, M.-W.; Andree, R.; Dollinger, M. (Bayer A.-G., Germany) Ger. Offen. DE 19632005 A1, 1998. (d) Koiso, T.; Ono, S.; Kondo, H.; Asada, T. (Dainippon Ink and Chemicals, Inc., Japan) Jpn. Kokai Tokkyo Kono JP 09241245, 1997. (e) Kameswaran, V. (American Cyanamid Co., USA) US 6191275 B1, 2001.
8. Yagi, K.; Akimoto, K.; Mimori, N.; Miyake, T.; Kudo, M.; Arai, K.; Ishii, S. Pest Manag. Sci. 2000, 56, 65-73.
9. Dolle, R. E. J. Comb. Chem. 2001, 3, 477-517 and references therein.
10. For recent reviews, see: (a) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
11. For recent reviews, see: (a) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
12. Presented in part (FLUO0006) at the 226th ACS National Meeting, Sept 7-11, 2003, New York.
13. Kotoris, C. C.; Chen, M.-J.; Taylor, S. J. Org. Chem. 1998, 63, 8052-8057.
14. Middleton, W. J.; Bingham, E. M. J. Org. Chem. 1980, 45, 2883-2887.
15. We obtained improved chemical yields for 6b (91 vs 61%) using 2.2 equiv of Deoxofluor (dimethoxyethylaminotrifluorosulfurane) at room temperature for 24 h instead of DAST. See: Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048-7054.
16. (a) Biaise, E. E. C. R. Hebd. Seances Acad. Sci. 1901, 132, 478.
17. (b) Cason, J.; Rinehart, K. L., Jr.; Thornton, S. D., Jr. J. Org. Chem. 1953, 18, 1594-1600.
18. (c) Kagan, H. B.; Suen, Y.-H. Bull. Soc. Chim. Fr. 1966, 1819-1822.
19. (d) Syed, J.; Förster, S.; Effenberger, F. Tetrahedron: Asymmetry 1998, 9, 805-815.
20. (e) Mauduit, M.; Kouklovsky, C.; Langlois, Y.; Riche C. Org. Lett. 2000, 2, 1053-1056.
21. (a) Hiyama, T.; Kobayashi, K. T. Tetrahedron Lett. 1982, 23, 1597-1600.
22. (b) Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833-3835.
23. (c) Lee, A. S.-Y.; Cheng, R.-Y. Tetrahedron Lett. 1997, 38, 443-446.
24. Fustero, S.; Salavert, E.; Sanz-Cervera, J. F.; Román, R.; Fernández-Gutiérrez, B.; Asensio, A. Lett. Org. Chem. 2004, 1, 93-98.
25. Wahhab, A.; Leban, J. Tetrahedron Lett. 2000, 41, 1487-1490.
26. See, for instance: (a) Vidal, A.; Nefzi, A.; Houghten, R. A. J. Org. Chem. 2001, 66, 8268-8272. (b) Volonterio, A.; Chiva, G.; Fustero, S.; Piera, J.; Sánchez Roselló, M.; Sani, M.; Zanda, M. Tetrahedron Lett. 2003, 44, 7019-7022.
27. See, for instance: (a) Vidal, A.; Nefzi, A.; Houghten, R. A. J. Org. Chem. 2001, 66, 8268-8272. (b) Volonterio, A.; Chiva, G.; Fustero, S.; Piera, J.; Sánchez Roselló, M.; Sani, M.; Zanda, M. Tetrahedron Lett. 2003, 44, 7019-7022.
28. Bräse, S.; Dahmen, S. In Handbook of Combinatorial Chemistry; Nicolau, K. C., Hanko, R., Hartwig, W., Eds; Wiley-VCH: Weinheim, 2002; Vol. 1, pp 59-169.