Download PDF
Synlett 2012; 23(4): 637-639
DOI: 10.1055/s-0031-1290160
letter
© Georg Thieme Verlag Stuttgart · New York

Expedient Microwave-Assisted Synthesis of Novel 6-Substituted 5-Alkoxy(benzyloxy)-3,6-dihydro-2H-1,3,4-oxadiazin-2-ones

Detlef Geffken*
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany, Fax: +49(40)428386573   Email: geffken@chemie.uni-hamburg.de
,
Finn K. Hansen
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany, Fax: +49(40)428386573   Email: geffken@chemie.uni-hamburg.de
,
Mehdi Khankischpur
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany, Fax: +49(40)428386573   Email: geffken@chemie.uni-hamburg.de
,
Tobias Mauz
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany, Fax: +49(40)428386573   Email: geffken@chemie.uni-hamburg.de
,
Ronald Meurer
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany, Fax: +49(40)428386573   Email: geffken@chemie.uni-hamburg.de
› Author Affiliations
Further Information

Publication History

Received: 14 October 2011

Accepted after revision: 04 January 2012

Publication Date:
03 February 2012 (online)

    Permissions and Reprints All articles of this category


Abstract

Novel 6-substituted 5-alkoxy(benzyloxy)-3,6-dihydro-2H-1,3,4-oxadiazin-2-ones have been prepared in good yields and very short reaction times by intramolecular cyclization of α-hydroxyhydrazonates in the presence of sodium ethoxide under microwave irradiation.

Key words

hydrazonates - nitrogen heterocycles - cyclization - microwave-assisted synthesis - ring closure

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References

    • 1a Caddick S, Fitzmaurice R. Tetrahedron 2009; 65: 3325
      Crossref
    • 1b De La Hoz A, Diaz-Ortiz A, Moreno A. Curr. Org. Chem. 2004; 8: 903
      Crossref
  • 2 Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
    CrossrefPubMed
  • 3 Wathey B, Tiemey J, Lidström P, Westman J. Drug Discov. Today 2002; 7: 373
    Crossref
  • 4 Lidström P, Tierney J, Wathey B, Westman J. Tetrahedron 2001; 57: 9225
    Crossref
    • 5a Ikizler A, Demirbas N, Ikizler AA. J. Heterocycl. Chem. 1996; 33: 1765
      Crossref
    • 5b Ikizler AA, Yildirim N. J. Heterocycl. Chem. 1998; 35: 377
      Crossref
  • 6 Malbec F, Milcent R, Barbier G. J. Heterocycl. Chem. 1984; 21: 1689
    Crossref
  • 7 Rigo B, Fasseur D, Cauliez P, Couturier D. Synth. Commun. 1989; 19: 2321
    Crossref
  • 8 For an excellent review, see: Shawali AS, Sherif SM. Curr. Org. Chem. 2007; 11: 773
    Crossref
    • 9a Wing KD. EP 361645, 1990 ; Chem. Abstr. 1990, 113, 151998
    • 9b Ishida S, Koike K. JP 48028421, 1973 ; Chem. Abstr. 1973, 79, 65812
    • 9c Nesvadba H. DE 2659528, 1977 ; Chem. Abstr. 1977, 87, 117863
    • 10a Yoshimoto T, Hosono A, Miki J, Oda K, Ura M, Sato N, Toyama T, Tachibana H, Enomoto Y, Funakoshi Y, Fujita T, Hojo Y. DE 2944783, 1980 ; Chem. Abstr. 1980, 93, 167904
    • 10b Gy ET. GB 1382781, 1975 ; Chem. Abstr. 1975, 83, 43386
  • 11 Khankischpur M, Hansen FK, Meurer R, Mauz T, Bergmann B, Walter RD, Geffken D. Arch. Pharm. Life Sci. 2011; 344: 755
  • 12 Pinner A. Die Imidoäther und ihre Derivate . Oppenheim; Berlin: 1892
    Google Scholar
  • 13 Kurz T, Khankischpur M, Widyan K. Tetrahedron Lett. 2006; 47: 4241
    Crossref
  • 14 CCDC 845877 contains the supplementary crystallographic data for the deposited structure. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif .