PDF herunterladen
Synthesis 2005(8): 1340-1344  
DOI: 10.1055/s-2005-865292
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel 4-Functionalised Oxazolidin-2-ones

Khalid Widyan, Thomas Kurz*
Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: kurz@chemie.uni-hamburg.de;
Weitere Informationen

Publikationsverlauf

Received 19 November 2004
Publikationsdatum:
07. April 2005 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The synthesis of O-substituted and O-unsubstituted 3-hydroxy-4-thioxo-oxazolidin-2-ones, functionalised 4-imino-oxazolidine-2-ones and 4-phenoxy-imino-oxazolidin-2-one starting from O-substituted and O-unsubstituted 3-hydroxy-4-imino-oxazolidin-2-ones is described. A one-pot protocol for the preparation of 4-methoxyimino-, 4-aralkoxyimino- and 4-phenoxyimino-oxazolidin-2-ones has been developed.

Key words

heterocycles - oxazolidin-2-ones - Dimroth rearrangement - thionation - ring closure

    References

  • 1a Tomlin CDS. The Pesticide Manual   12th ed.:  BCPC Publications; Alton UK: 2000.  p.375 
    Google Scholar
  • 1b Sternberg JA. Geffken D. Adams JB. Jordan DB. Sternberg CG. Campbell CL. Moberg WK. Livingston RS. Synthesis and Chemistry of Agrochemicals, ACS Symposium Series 686   American Chemical Society; Washington DC: 1998.  p.216 
    Google Scholar
  • 2 Tomlin CDS. The Pesticide Manual   12th ed.:  BCPC Publications; Alton UK: 2000.  p.956 
    Google Scholar
  • 3 Thueson DO. Withrow CD. Giam CS. Woodbury DM. Epilepsia  1974,  15:  563 
    CrossrefGoogle Scholar
  • 4a Geffken D. Riederer C. Sci. Pharm.  2001,  69:  265 
    Google Scholar
  • 4b Riederer C. PhD Dissertation: Zur Synthese von Tetrahydro-oxazolo-[4,3-c]-1,2,4-oxadiazol-5-onen und Tetrahydro-oxazolo-[4,3-c]-1,2,4-oxadiazin-6-onen aus 4-Hydroxyimino-oxazolidin-2-onen   Universität Hamburg; Germany: 1999. 
    Google Scholar
  • 5 Sternberg JA, and Adams JB. inventors; DuPont de Nemours, EP  503798.  ; Chem. Abstr. 1993, 118 , 80921u
  • 6 Kurz T. Widyan K. Org. Lett.  2004,  6:  4403 
    CrossrefGoogle Scholar
  • 7 Kurz T. Geffken D. Widyan K. Tetrahedron  2004,  60:  2409 
    CrossrefGoogle Scholar
  • 8 Kurz T. Widyan K. Wackendorff C. Schlüter K. Synthesis  2004,  1987 
    Artikel in Thieme ConnectGoogle Scholar
  • 9 Kurz T. Widyan K. Org. Biomol. Chem.  2004,  2:  2023 
    CrossrefGoogle Scholar