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

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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.

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Authors and Affiliations

  1. Department of Environmental Pollution, Environmental Sciences Research Institute, Shahid Beheshti University, G.C. Evin, 1983963113, Tehran, Iran

    Morteza Mehrdad

  2. Department of Chemistry, Shahid Beheshti University, G.C. Evin, 1983963113, Tehran, Iran

    Laleh Faraji, Khosrow Jadidi, Parisa Eslami & Hossein Sureni

Authors
  1. Morteza Mehrdad
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  2. Laleh Faraji
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  3. Khosrow Jadidi
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  4. Parisa Eslami
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  5. Hossein Sureni
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Correspondence to Morteza Mehrdad.

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Mehrdad, M., Faraji, L., Jadidi, K. et al. A regioselective and diastereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition of stable isatin ketonitrone and various dipolarophiles. Monatsh Chem 142, 917–921 (2011). https://doi.org/10.1007/s00706-011-0518-2

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  • DOI: https://doi.org/10.1007/s00706-011-0518-2

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