Synthesis of new 3-(1-ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl (or 5-phenyl)-1,5-dihydro-pyrrol-2-ones Starting from γ-Keto thioesters and amines

Synthesis

Volumn , Issue 5, 2004, Pages 711-721

  Bouillon, Jean Philippe ^a   Tinant, Bernard ^b   Nuzillard, Jean Marc ^a   Portella, Charles ^a  

^a CNRS   (France)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Fluorine; Lactam; Nitrogen heterocycles; Pyrrol 3 one

Indexed keywords

ESTERS; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS; X RAY DIFFRACTION;

COMPUTER-ASSISTED ELUCIDATION; SUBSTITUTION PATTERN; UNSATURATED LACTAMS;

SYNTHESIS (CHEMICAL);

AMINE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; THIOESTER;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPUTER ANALYSIS; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 1942489199     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815970     Document Type: Article

References (26)

1. Muzard, M.; Portella, C. J. Org. Chem. 1993, 58, 29.
2. Huot, J.-F.; Muzard, M.; Portella, C. Synlett 1995, 247.
3. Hénin, B.; Huot, J.-F.; Portella, C. J. Fluorine Chem. 2001, 107, 281.
4. (a) Biomedicinal Aspects of Fluorine Compounds; Filler, R.; Kobayashi, Y., Eds.; Elsevier: New York, 1982.
5. (b) Welch, J. T. Tetrahedron 1987, 43, 3123.
6. (c) Fluorine in Bioorganic Chemistry; Welch, J. T.; Eswarakrishnan, S., Eds.; John Wiley & Sons: New York, 1991.
7. (a) Hewitt, C. D.; Silvester, M. J. Aldrichimica Acta 1988, 21, 3.
8. (b) Differding, E.; Frick, W.; Lang, R. W.; Martin, P.; Schmit, C.; Veenstra, S.; Greuter, H. Bull. Soc. Chim. Belg. 1990, 99, 647.
9. (c) Silvester, M. J. Aldrichimica Acta 1991, 24, 31.
10. (d) Silvester, M. J. Aldrichimica Acta 1995, 28, 45.
11. Brulé, C.; Bouillon, J.-P.; Nicolaï, E.; Portella, C. Synthesis 2003, 436.
12. Bouillon, J.-P.; Hénin, B.; Huot, J.-F.; Portella, C. Eur. J. Org. Chem. 2002, 1556.
13. (a) Kurita, J.; Kojima, H.; Tsuchiya, T. Heterocycles 1984, 22, 721.
14. (b) Iwasawa, N.; Maeyama, K. J. Org. Chem. 1997, 62, 1918.
15. (c) Ghelfi, F.; Stevens, C. V.; Laureyn, I.; Van Meenen, E.; Rogge, T. M.; De Buyck, L.; Nikitin, K. V.; Grandi, R.; Libertini, E.; Pagnoni, U. M.; Schenetti, L. Tetrahedron 2003, 59, 1147.
16. (d) Clark, A. J.; Dell, C. P.; McDonagh, J. M.; Geden, J.; Mawdsley, P. Org. Lett. 2003, 5, 2063.
17. (e) Yeung, B. K. S.; Boger, D. L. J. Org. Chem. 2003, 68, 5249.
18. (a) Lightner, D. A.; Low, L. K. J. Heterocycl. Chem. 1972, 9, 167.
19. (b) Arzoumanian, H.; Jean, M.; Nuel, D.; Garcia, J. L.; Rosas, N. Organometallics 1997, 16, 2726.
20. (a) Farina, F.; Martin, M. V.; Paredes, M. C. Synthesis 1973, 167.
21. (b) Shiraki, R.; Sumino, A.; Tadano, K.-I.; Ogawa, S. Tetrahedron Lett. 1995, 36, 5551.
22. (c) Kotera, M.; Roupioz, Y.; Defrancq, E.; Bourdat, A.-G.; Garcia, J.; Coulombeau, C.; Lhomme, J. Chem.-Eur. J. 2000, 6, 4163.
23. Nuzillard, J.-M.; Connolly, J. D.; Delaude, C.; Richard, B.; Zèches-Hanrot, M.; Le Men-Olivier, L. Tetrahedron 1999, 55, 11511.
24. Spek, A. PLATON: Molecular Geometry Program; University of Utrecht: The Netherlands, 1998.
25. Bouillon, J.-P.; Didier, B.; Dondy, B.; Doussot, P.; Plantier-Royon, R.; Portella, C. Eur. J. Org. Chem. 2001, 187.
26. Sheldrick, G. M. SHELXS-97 and SHELXL-97: Program for the Solution and Refinement of Crystal Structures; University of Göttingen: Germany, 1997.