One Pot Synthesis of Fluoroalkyl Pyrimidines from α-Fluoroalkyl Carbonyl Compounds, Orthoesters and Ammonium Carbonate

Synlett

Volumn 1997, Issue 11, 1997, Pages 1261-1262

  Luo, Bing Hao ^a   Guan, Hui Ping ^a   Hu, Chang Ming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002702336     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1031     Document Type: Article

References (18)

1. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
2. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
3. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
4. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
5. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
6. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
7. Welch, J. T. Tetrahedron, 1987, 43, 3123; Filler, R. and Kobayashi, Y. Biomedicinal Aspect of Fluorine Chemistry, Kokansha, Tokyo, 1983; Liebman, J. F.; Greenberg, A. and Dolbier, W. R. Jr., Fluorine-containing Molecules, Structure, Reactivity, Synthesis and Application, VCH, New York, 1988. Lang, R. W. Helv. Chem. Acta, 1986, 69, 881; Fuijita, M.; Hiyama, T. and Kondo, K. Tetrahedron Lett., 1986, 27, 2139; Fuijita, M.; Hiyama, T. Tetrahehron Lett., 1986, 27, 3655; McClinton, M. A. and McClinton, D. A. Tetrahedron, 1992, 48, 6555.
8. Examples: Yamazaki, T.; Mizutami, K. and Kitazume, T. J. Org. Chem., 1995, 60, 6046; Ranachandran, P. V.; Gong, B. and Brown, H. C. J. Org. Chem., 1995, 60, 41; Beguw, J. P., Benayoud F. and Bonnet-Delpon, D. J. Org Chem., 1995, 60, 5029; Makino, Y.; Iseki, K.; Fujuu, K.; Oishi, S.; Hirano, F. and Kobayashi, Y. Tetrahedron Lett., 1995, 36, 6527.
9. Examples: Yamazaki, T.; Mizutami, K. and Kitazume, T. J. Org. Chem., 1995, 60, 6046; Ranachandran, P. V.; Gong, B. and Brown, H. C. J. Org. Chem., 1995, 60, 41; Beguw, J. P., Benayoud F. and Bonnet-Delpon, D. J. Org Chem., 1995, 60, 5029; Makino, Y.; Iseki, K.; Fujuu, K.; Oishi, S.; Hirano, F. and Kobayashi, Y. Tetrahedron Lett., 1995, 36, 6527.
10. Examples: Yamazaki, T.; Mizutami, K. and Kitazume, T. J. Org. Chem., 1995, 60, 6046; Ranachandran, P. V.; Gong, B. and Brown, H. C. J. Org. Chem., 1995, 60, 41; Beguw, J. P., Benayoud F. and Bonnet-Delpon, D. J. Org Chem., 1995, 60, 5029; Makino, Y.; Iseki, K.; Fujuu, K.; Oishi, S.; Hirano, F. and Kobayashi, Y. Tetrahedron Lett., 1995, 36, 6527.
11. Examples: Yamazaki, T.; Mizutami, K. and Kitazume, T. J. Org. Chem., 1995, 60, 6046; Ranachandran, P. V.; Gong, B. and Brown, H. C. J. Org. Chem., 1995, 60, 41; Beguw, J. P., Benayoud F. and Bonnet-Delpon, D. J. Org Chem., 1995, 60, 5029; Makino, Y.; Iseki, K.; Fujuu, K.; Oishi, S.; Hirano, F. and Kobayashi, Y. Tetrahedron Lett., 1995, 36, 6527.
12. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Chem. Commun, 1994, 631. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Perhin Trans. I, 1994, 2161. Tang, X. Q.; Hu, C. M. J. Fluorine Chem., 1995, 74, 9. Guan, H. P.; Hu, Q. S.; Hu, C. M. Synthesis, 1996, 997. Guan, H. P.; Luo, B. H.; Hu, C. M. Synthesis, 1997, 461.
13. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Chem. Commun, 1994, 631. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Perhin Trans. I, 1994, 2161. Tang, X. Q.; Hu, C. M. J. Fluorine Chem., 1995, 74, 9. Guan, H. P.; Hu, Q. S.; Hu, C. M. Synthesis, 1996, 997. Guan, H. P.; Luo, B. H.; Hu, C. M. Synthesis, 1997, 461.
14. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Chem. Commun, 1994, 631. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Perhin Trans. I, 1994, 2161. Tang, X. Q.; Hu, C. M. J. Fluorine Chem., 1995, 74, 9. Guan, H. P.; Hu, Q. S.; Hu, C. M. Synthesis, 1996, 997. Guan, H. P.; Luo, B. H.; Hu, C. M. Synthesis, 1997, 461.
15. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Chem. Commun, 1994, 631. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Perhin Trans. I, 1994, 2161. Tang, X. Q.; Hu, C. M. J. Fluorine Chem., 1995, 74, 9. Guan, H. P.; Hu, Q. S.; Hu, C. M. Synthesis, 1996, 997. Guan, H. P.; Luo, B. H.; Hu, C. M. Synthesis, 1997, 461.
16. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Chem. Commun, 1994, 631. Tang, X. Q.; Hu, C. M. J. Chem. Soc. Perhin Trans. I, 1994, 2161. Tang, X. Q.; Hu, C. M. J. Fluorine Chem., 1995, 74, 9. Guan, H. P.; Hu, Q. S.; Hu, C. M. Synthesis, 1996, 997. Guan, H. P.; Luo, B. H.; Hu, C. M. Synthesis, 1997, 461.
17. 2: C, 55.56, H, 5.09, N, 12.96, F, 26.39. Found: C, 54.84, H, 5.73, N, 12.35, F, 26.46.
18. 3NO: C, 49.74, H, 5.18, N, 7.25, F, 29.53. Found: C, 50.27, H, 5.27, N, 7.24, F, 29.16.