Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 9, pp 917–921

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

Authors

    • Department of Environmental Pollution, Environmental Sciences Research InstituteShahid Beheshti University
  • Laleh Faraji
    • Department of ChemistryShahid Beheshti University
  • Khosrow Jadidi
    • Department of ChemistryShahid Beheshti University
  • Parisa Eslami
    • Department of ChemistryShahid Beheshti University
  • Hossein Sureni
    • Department of ChemistryShahid Beheshti University
Original Paper

DOI: 10.1007/s00706-011-0518-2

Cite this article as:
Mehrdad, M., Faraji, L., Jadidi, K. et al. Monatsh Chem (2011) 142: 917. doi:10.1007/s00706-011-0518-2

Abstract

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

https://static-content.springer.com/image/art%3A10.1007%2Fs00706-011-0518-2/MediaObjects/706_2011_518_Figa_HTML.gif

Keywords

Isatin ketonitrone1,3-Dipolar cycloadditionIonic liquidsSpiro[oxindole-isoxazolidine] derivatives

Copyright information

© Springer-Verlag 2011