Water-Promoted Ring-Opening Reactions of N-Substituted Saccharins and Phthalimides by Amines

Authors

  • Lisha Bai,

    1. Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China
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  • Xuan Zhang,

    1. Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China
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  • Ning Ma

    Corresponding author
    1. Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China
    2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
    • Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China, Tel.: 0086-022-27403475; Tax: 0086-022-27403475

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Abstract

The reactions of N-substituted saccharins and phthalimides with amines were promoted by water. Various o-sulfamoyl benzamides and N,N′-disubstituted phthalamides were prepared in moderate to good yields. These reactions have prominent advantages, such as short reaction time, less by-products and simple isolation of the products. Water can probably stabilize the reaction intermediates and facilitate precipitation of the ring-opening products. When steric hindrance arose, hydrolytic compounds, either free acid or salts of the acids, were obtained. Possible reason for the formation of amine salts of o-sulfamoyl benzoic acids was proposed.

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