A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts |
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| Authors: | Ahmad Reza Massah Beheshteh Asadi Azadeh Molseghi Hamid Javaherian Naghash |
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| Institution: | a Department of Chemistry, Islamic Azad University, Shahreza Branch, Shahreza, P.O. Box: 86145-311, Isfahan, Iran
b Razi Chemistry Research Center, Islamic Azad University, Shahreza Branch, Shahreza, Isfahan, Iran |
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| Abstract: | Some metal hydrogen sulfates were used as acid catalysts in the N-acylation of different sulfonamides using carboxylic acid chlorides and anhydrides as acylating agents under both heterogeneous and solvent-free conditions. Al(HSO4)3 and Zr(HSO4)4 were found to have the highest activity and catalyze the reactions efficiently to furnish the primary N-acyl sulfonamides (RCONHSO2R′), secondary N-acylsulfonamides (RCONR″SO2R′) and bis-N-acylsulfonamnides RCO(SO2R′)N-R″-N(SO2R′)COR] in good to high yield. The mild reaction conditions, inexpensive and low toxicity of catalysts and easy work-up procedure make this method attractive. |
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| Keywords: | N-Acylation N-Acylsulfonamide Aluminum hydrogen sulfate Zirconium hydrogen sulfate Solvent-free reactions Heterogeneous catalysis |
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