Original Paper

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

  • Morteza MehrdadAffiliated withDepartment of Environmental Pollution, Environmental Sciences Research Institute, Shahid Beheshti University Email author 
  • , Laleh FarajiAffiliated withDepartment of Chemistry, Shahid Beheshti University
  • , Khosrow JadidiAffiliated withDepartment of Chemistry, Shahid Beheshti University
  • , Parisa EslamiAffiliated withDepartment of Chemistry, Shahid Beheshti University
  • , Hossein SureniAffiliated withDepartment of Chemistry, Shahid Beheshti University

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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

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

Keywords

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