Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 9, pp 917–921 | Cite as

A regioselective and diastereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition of stable isatin ketonitrone and various dipolarophiles

  • Morteza Mehrdad
  • Laleh Faraji
  • Khosrow Jadidi
  • Parisa Eslami
  • Hossein Sureni
Original Paper


The 1,3-dipolar cycloaddition of stable isatin ketonitrone with various dipolarophiles has been conducted under classical, ionic liquid, and solvent-free conditions to give novel spiro[oxindole-isoxazolidine] derivatives with similar diastereoselectivity. In the presence of the ionic liquid 1-butyl-3-methylimidazolium bromide highly diastereoselective and regioselective cyclocondensation products were obtained in good to excellent yields in the absence of any catalyst. The reaction workup was simple and the ionic liquid was easily recovered from the reaction and reused.

Graphical abstract


Isatin ketonitrone 1,3-Dipolar cycloaddition Ionic liquids Spiro[oxindole-isoxazolidine] derivatives 


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Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Morteza Mehrdad
    • 1
  • Laleh Faraji
    • 2
  • Khosrow Jadidi
    • 2
  • Parisa Eslami
    • 2
  • Hossein Sureni
    • 2
  1. 1.Department of Environmental Pollution, Environmental Sciences Research InstituteShahid Beheshti UniversityTehranIran
  2. 2.Department of ChemistryShahid Beheshti UniversityTehranIran

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