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A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides

Abstract

The novel functionalized N,N′-[2-(arylsulfonamido)propane-1,3-diyl]bis(N-allylarylsulfonamide) and N,N′-[2-(methylsulfonamido)propane-1,3-diyl]bis(N-benzylarylsulfonamide) derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using substituted arylsulfonamides in the presence of sodium methoxide under catalyst-free condition in good yields.

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Acknowledgements

We thank the Bushehr Branch, Islamic Azad University for support.

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Correspondence to Gholamhossein Khalili.

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Azizi, F., Khalili, G. A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides. Monatsh Chem 151, 261–265 (2020). https://doi.org/10.1007/s00706-019-02546-9

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Keywords

  • 2-(Bromomethyl)-1-sulfonylaziridines
  • Ring opening reaction
  • 1,3-Difunctionalized 2-aminopropane
  • N-Activated aziridines
  • Arylsulfonamide