A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts
作者:Ahmad Reza Massah、Beheshteh Asadi、Mahdieh Hoseinpour、Azadeh Molseghi、Roozbeh Javad Kalbasi、Hamid Javaherian Naghash
DOI:10.1016/j.tet.2009.06.112
日期:2009.9
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. (C) 2009 Elsevier Ltd. All rights reserved.