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Synthesis 2007(10): 1453-1455  
DOI: 10.1055/s-2007-966028
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Alkoxy-5,6-dihydro-4H-1,2,5-oxadiazines from Alkyl α-Aminohydroximates

Thomas Kurz*, Wolfgang Thimann, Detlef Geffken
Institute of Pharmacy, University of Hamburg, Bundesstraße 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: kurz@chemie.uni-hamburg.de;
Further Information

Publication History

Received 23 January 2007
Publication Date:
02 May 2007 (online)

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Abstract

The synthesis of previously unreported 3-alkoxy-5,6-dihydro-4H-1,2,5-oxadiazines starting from alkyl α-aminohydrox­imates is described.

Key words

heterocycles - ring closure - carbonylations - thiocarbonylations

    References

  • 1a Dunn G. Elvidge JA. Newbold GT. Ramsay DWC. Spring FS. Sweeny W. Nature (London)  1949,  164:  181 
    Google Scholar
  • 1b Knobler Y. Bittner S. Frankel M. J. Chem. Soc.  1964,  3491 
    Google Scholar
  • 2a O’Sullivan P. Glennon JD. Farkas E. Kiss T. J. Coord. Chem.  1996,  38:  271 
    Google Scholar
  • 2b Meier C. Boche G. Chem. Ber.  1990,  123:  1691 
    Google Scholar
  • 2c Ono M. Itoh I. Tetrahedron Lett.  1989,  30:  207 
    Google Scholar
  • 2d Geffken D. Ploetz A. von Zydowitz H. Sci. Pharm.  2002,  70:  325 ; Chem. Abstr. 2002, 139, 68920
    Google Scholar
  • 2e Geffken D. von Zydowitz H. Ploetz A. Z. Naturforsch.  2005,  60b:  967 
    Google Scholar
  • 3a Coletti-Previero M.-A. Crastes de Paulet A. Matras H. Previero A. Biochem. Biophys. Res. Commun.  1982,  107:  465 
    CrossrefGoogle Scholar
  • 3b Smith RA. Coles PJ. Spencer RW. Copp LJ. Jones CS. Krantz A. Biochem. Biophys. Res. Commun.  1988,  155:  1201 
    CrossrefGoogle Scholar
  • 3c Smissman EE. Warner VD. J. Med. Chem.  1972,  15:  681 
    CrossrefGoogle Scholar
  • 4 Geffken D. Thimann W. Z. Naturforsch.  2001,  56b:  547 
    Google Scholar
  • 5a Geffken D. Schwarz G. Arch. Pharm. (Weinheim)  1988,  321:  45 
    Google Scholar
  • 5b Schwarz G. Geffken D. Liebigs Ann. Chem.  1988,  35 
    Google Scholar
  • 6 Gnichtel H. Thiele S. Chem. Ber.  1971,  104:  1507 
    CrossrefGoogle Scholar
  • 7 Gnichtel H. Exner S. Bierbüße H. Alterdinger M. Chem. Ber.  1971,  104:  1512 
    CrossrefGoogle Scholar