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Reactivity in [4+2] Cycloadditions of New 4-trifluoromethyl-1,3-oxazin-6-ones - Access To Functionalized 2-trifluoromethyl Pyridines

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Evariste, F. Janousek, Z. Maliverney, C. Merenyi, R. Viehe, HG.

Recently discovered 4-trifluoromethyl-1,3-oxazin-6-ones react with electron-poor dienophiles as 2-aza-1,3-dienes in Diels-Alder cycloadditions to give new 2-trifluoromethyl pyridines (3a-d, 4a-c). Regioselectivity is excellent in the case of unsymmetrical dienophiles. These new pyridines permit further useful transformations.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 1993
Language Anglais
Journal information "Journal fuer Praktische Chemie. Chemiker-Zeitung" - Vol. 335, no. 1, p. 35-41 (1993)
Peer reviewed yes
Publisher Johann Ambrosius Barth Verlag (Heidelberg)
issn 0941-1216
Publication status Publié
Affiliation UCL
Links
  1. Decock-Plancquaert Marie-Aimée, Evariste François, Guillot Nadine, Janousek Zdenek, Maliverney Christian, Merényi Robert, Viehe Heinz G., Syntheses of New 4-Trifluoromethylated 1,3-Oxazin-6-Ones from the Enamine of Ethyl Trifluoroacetoacetate, 10.1002/bscb.19921010412
  2. Boger, Tetrahedron, 39, 2869 (1983)
  3. Steglich, Gazz. Chim. Ital., 116, 361 (1986)
  4. Steglich, Angew. Chem. Int. Ed., 13, 533 (1974)
  5. Buschbaum, Angew. Chem., Int. Ed., 13, 484 (1974)
  6. Höfle, Angew. Chem., Int. Ed., 11, 720 (1972)
  7. Hollitzer, Angew. Chem., Int. Ed., 12, 197 (1973)
Bibliographic reference Evariste, F. ; Janousek, Z. ; Maliverney, C. ; Merenyi, R. ; Viehe, HG.. Reactivity in [4+2] Cycloadditions of New 4-trifluoromethyl-1,3-oxazin-6-ones - Access To Functionalized 2-trifluoromethyl Pyridines. In: Journal fuer Praktische Chemie. Chemiker-Zeitung, Vol. 335, no. 1, p. 35-41 (1993)
Permanent URL http://hdl.handle.net/2078.1/49845