Convenient one-pot synthesis of fluorinated DHPs derivatives and their further transformations

Tetrahedron Letters

Volumn 51, Issue 30, 2010, Pages 3975-3977

  Wang, Pengyuan ^a   Song, Liping ^a,b   Yi, Hai ^a   Zhang, Min ^a   Zhu, Shizheng ^b   Deng, Hongmei ^a   Shao, Min ^a  

^a SHANGHAI UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; ETHYL 4,4,4 TRIFLUORO 1,3 DIOXOBUTANOATE; PIPERIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FLUORINATION; MICHAEL ADDITION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; X RAY DIFFRACTION;

TRIFLUORO;

EID: 77953686168     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.110     Document Type: Article

References (44)

1. Hiyama T. Organofluorine Compounds (2000), Springer, Berlin
2. Hudlicky M. Chemistry of Organic Fluorine Compounds. 2nd ed. (1976), Ellis Harwood, Chichester
3. In: Welch J.T., and Eswarakrishnan S. (Eds). Fluorine in Bioorganic chemistry (1991), Wiley, New York
4. Prabhakaran J., Underwood M.D., Parsey R.V., Arango V., Majo V.J., Simpson N.R., Heertum R.V., Mann J.J., and Kumar J.S.D. Bioorg. Med. Chem. 15 (2007) 1802-1807
5. Filler R., and Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry (1982), Kodansha & Elsevier Biomedical, Tokyo
6. Filler R., Kobayashi Y., and Yagupolskii L.M. Organofluorine Compounds in Medical Chemistry and Boimedical Application (1993), Elsevier, Amsterdam
7. In: Abraham D.J. (Ed). Burger's Medicinal Chemistry and Drug Discovery Vol. 1 (2003), John Wiley and Sons, New York
8. Ismail F.M.D. J. Fluorine Chem. 118 (2002) 27-33
9. Welch J.T., and Ewarakrishnan S.E. Fluorine in Bioorganic Chemistry (1991), John Wiley, New York
10. Becker A. Inventory of Industrial Fluoro-Biochemicals (1996), Eyrolles, Paris
11. Lavilla R. J. Chem. Soc., Perkin Trans. 1 (2002) 1141-1156
12. Sausins A., and Duburs G. Heterocycles 27 (1988) 269-289
13. Meguro K., Aizawa M., Sohda T., Kawamatsu Y., and Nagaoka A. Chem. Pharm. Bull. 33 (1985) 3787-3797
14. Triggle D.J. Cell. Mol. Neurobiol. 23 (2003) 293-303
15. De Simone R.W., Currie K.S., Mitchell S.A., Darrow J.W., and Pippin D.A. Comb. Chem. 7 (2004) 473-493
16. Loev B., Ehrreich S.J., and Tedeschi R.E. J. Pharm. Pharmacol. 24 (1972) 917-918
17. Harrold M. In: Williams D.A., and Lemke T.L. (Eds). Foye's Principles of Medicinal Chemistry. 5th ed. (2002), Lippin-cott Williams and Wilkins, Baltimore 533-561
18. Mojarrad J.S., Vo D., Velázquez C., and Knaus E.E. Bioorg. Med. Chem. 13 (2005) 4085-4091
19. Bossert F., Meyer H., and Wehinger E. Angew. Chem., Int. Ed. 20 (1981) 762-769
20. Stout D.M., and Meyers A.I. Chem. Rev. 82 (1982) 223-243
21. Janis R.A., Silver P.J., and Triggle D.J. Adv. Drug Res. 16 (1987) 309-591
22. Bossert F., and Vater W. Med. Res. Rev. 9 (1989) 291-324
23. Marchalin S., Chudik M., Mastihuba V., and Decroix B. Heterocycles 48 (1998) 1943-1958
24. Achiwa K., and Kato T. Curr. Org. Chem. 3 (1999) 77-106
25. Schramm M., Thomas G., Towan I.L., and Franckowiak G. Nature 303 (1983) 535-537
26. Brown A.M., Kunz¢ D.L., and Yatani A. Nature 311 (1984) 570-572
27. Chorvat R.J., and Rorig K.J. J. Org. Chem. 53 (1988) 5779-5781
28. Kappe C.O. Tetrahedron 49 (1993) 6937-6963
29. Kappe C.O., and Fabian W.M.F. Tetrahedron 53 (1997) 2803-2816
30. Song L.P., Li X.F., Xing C.H., Li D.M., Zhu S.Z., Deng H.M., and Shao M. Synlett 5 (2010) 830-834
31. Dai B.F., Song L.P., Wang P.Y., Yi H., Jin G.F., Zhu S.Z., and Shao M. Synlett 11 (2009) 1842-1846
32. Song S.D., Song L.P., Dai B.F., Yi H., Jin G.F., Zhu S.Z., and Shao M. Tetrahedron 64 (2008) 5728-5735
33. Li D.M., Song L.P., Li X.F., Xing C.H., Peng W.M., and Zhu S.Z. Eur. J. Org. Chem. (2007) 3520-3525
34. Li D.M., Song L.P., Song S.D., and Zhu S.Z. J. Fluorine Chem. 128 (2007) 952-957
35. Li X.F., Song L.P., Xing C.H., Zhao J.W., and Zhu S.Z. Tetrahedron 62 (2006) 2255-2263
36. 4, filtered, and concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel using petroleum ether/ethyl acetate, 10:1(v/v) as eluent to give the pure product 5a 221.0 mg, 67% yield.
37. 4: C, 54.38; H, 4.87; N, 4.23. Found: C, 54.13; H, 4.87; N, 4.13.
38. CCDC-765386 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
39. Zhu S.Z., Song L.P., Jin G.F., Dai B.F., and Hao J. Curr. Org. Chem. 13 (2009) 1015-1027
40. Světlik J., Goljer I., and Tureček F. J. Chem. Soc., Perkin. I (1990) 1315-1318
41. Ochoa E., Suárez M., Verdecia Y., Pita B., Martin N., Quinteiro M., Seoane C., Soto J.L., Duque J., and Pomés R. Tetrahedron 54 (1998) 12409-12420
42. Rodriguez H., Suarez Z., Pérez R., Petit A., and Loupy A. Tetrahedron Lett. 44 (2003) 3709-3712
43. 3 (8.0 mL) was refluxed (62 °C) for indicated hours until completion of the reaction (monitored by TLC). The solvent was removed by rotavapor and the residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate 8:1 (v/v) as eluent to afford the pure product 6a 253.0 mg, 81% yield.
44. 3: C, 57.51; H, 4.50; N, 4.47. Found: C, 57.72; H, 4.49; N, 4.36.