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Synfacts 2006(10): 0991-0991
DOI: 10.1055/s-2006-949355
DOI: 10.1055/s-2006-949355
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Fluoropyridines from 4-(2-Fluoroallyl)oxazolones
U. Wittmann, F. Tranel, R. Fröhlich, G. Haufe*
Westfälische Wilhelms-Universität Münster, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. September 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200610/lookinside/thumbnails/10.1055-s-2006-949355-1.jpg)
Significance
The synthesis of polysubstituted 4-fluoropyridines from fluorinated amino acid allylic esters involving successive Ireland-Claisen (A) and aza-Cope (B) rearrangements of oxazolone derivatives in modest yields is reported. None of the intermediates suggested in the mechanism shown could be isolated although an analogous species to the carbene (C) has been trapped with dimethyl acetylenedicarboxylate (J. Fischer, W. Steglich Angew. Chem., Int. Ed. Engl. 1979, 18, 167-168). 4-Methyl oxazolones do not lead to fluoropyridine derivatives.