Reaction of thioglycolate with α-fluoro-β-(phenylthio)enones (or -enals): Synthesis of substituted α-carboxy-γ-fluorothiophenes

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1049-1052

  Andrès, Didier F ^a   Laurent, Eliane G ^a   Marquet, Bernard S ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; FLUORINATION; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562049     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02509-9     Document Type: Article

References (17)

1. 1) a) Silvester, M.J. "Recent Advances in Fluoroheterocyclic Chemistry" in Adv. Heterocycl. Chem. 1994, 59, 1-38.
2. b) Burger, K.; Wucherpfennig, U.; Brunner, E. "Fluoro Heterocycles with five-Membered Ring" in Adv. Heterocycl. Chem. 1994, 60, 1-64.
3. 2) For a review about syntheses and applications of 3-substituted thiophenes, see: Schulz, E.; Fahmi., K.; Lemaire M. Acros Chimica Acta 1994, 1, 1-16.
4. 3) Roncali, J. Chem. Rev. 1992, 92, 711-38.
5. 4) El Kassmi, A.; Fache, F.; Lemaire, M. J. Electroanal. Chem. 1994, 373, 241-44.
6. 5) a) Reinecke, M.G.; Pedaja, P, "Thiophene and its derivatives" in Heterocyclic Compounds, (Ed. Gronowitz, S), Wiley J. And Sons, New York, 1986, vol 44 (2), 79.
7. b) Cerichelli, G.; Crestoni, M.E.; Fornarini, S. Gazz. Chem. Ital. 1990 120 (12), 749-55.
8. 6) see ref.5a p 161-8.
9. 7) El Kassmi, A.; Fache, F.; Lemaire, M. Synt. Commun. 1994, 24, 95-101.
10. 8) a) Alberola, A.; Andres, J.M.; Gonzales, A.; Pedrosa, R.; Pradanos, P. Synt.Commun. 1990, 20, 2537-47.
11. b) Same reactions from β-chloro enals: Von Hauptmann, S.; Werner, E.M. J. Prakt. Chem. 1972, 314,499-506.
12. 9) α-Fluoro-β-phenylthio enones (or -enals) 1F were readily obtained by electrodifluorination of α,β-unsaturated vinyl sulfides 1H followed by the dehydrofluorination of the intermediate difluorosulfide during work-up: Andres, D.; Dietrich U.; Laurent, E.; Marquet, B. Tetrahedron, under press. (equation presented)
13. 10) Similar dithianyl derivatives have been recently postulated as intermediates to explain the mechanism of the reaction of 3-bromo-2-isocyanoacrylates (BICA) with benzylhydrosulfide: Yamada, M.; Fukui, T.; Nunami, K. Tetrahedron lett. 1995, 36, 257-60.
14. +, 31), 160 (21), 133 (25), 132 (24), 119 (87), 89 (11), 59 (17), 46 (11), 45 (52), 43 (100).
15. 12) Perlmutter, P.,"Conjugate Addition Reactions in Organic Syntheses", Tetrahedron Organic Chemistry Series (Editors: Baldwin, J.E. and Magnus, P.D), Pergamon Press, Oxford, New York, 1992, Vol. 9, 13 and cited references therein.
16. CF=3.0).
17. 14) Bernasconi, C.; Killion, R.; Fassberg, J.; Rappoport, Z. J. Am.Chem. Soc. 1989, 111, 6862-64.