Synthesis, characterization, and antimicrobial evaluation of sulfonamides containing N-acyl moieties catalyzed by bismuth(III) salts under both solvent and solvent-free conditions
Efficient N-acylation of sulfonamides with both readily available carboxylic acid chlorides and anhydrides has been carried out with catalysis by bismuth(III) salts including BiCl3 and Bi (OTf)3. The reactions proceed rapidly in both heterogeneous and solvent-free conditions and afforded the corresponding N-acylsulfonamides in good to excellent yields. The mild reaction conditions and low toxicity of bismuth salts make this procedure attractive and in close agreement with the goals of green chemistry. Some of the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of Gram-positive (Staphylococcus aureus ATCC 25922, clinical strains of Staphylococcus aureus VISA and Enterococcus spp.) and Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853, clinical strains of Klebsiella pneumonia and Escherichia coli) and as antifungal agents against Candida albicans (clinically isolated) by both disc diffusion and minimal inhibition concentration (MIC) methods. All these bacteria and fungi studied were screened against some antibiotics to compare with our chemicals' zone diameters.
Adibi, Hadi,Massah, Ahmad Reza,Majnooni, Mohammad Bagher,Shahidi, Sherita,Afshar, Maryam,Abiri, Ramin,Naghash, Hamid Javaherian
experimental part
p. 2753 - 2766
(2010/10/21)
HCIO4-SiO2 and NaHSO4-SiO2: Two efficient heterogeneous catalysts for synthesis of N-Acylsulfonamides under solvent-free conditions
A simple and efficient synthesis of N-acylsulfonamides has been accomplished by the reaction of sulfonamides with anhydrides under solvent-free conditions in the presence of HClO4-SiO2 or NaHSO4-SiO2.copy;2009. Bentham Science Publis
Liqiang, Wu,Chunguang, Yang,Chong, Zhang,Liming, Yang
experimental part
p. 234 - 236
(2010/04/23)
A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts
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
Massah, Ahmad Reza,Asadi, Beheshteh,Hoseinpour, Mahdieh,Molseghi, Azadeh,Kalbasi, Roozbeh Javad,Javaherian Naghash, Hamid
experimental part
p. 7696 - 7705
(2009/12/04)
Facile synthesis of N-acylsulfonamide in the presence of silica chloride (SiO2-Cl) both under heterogeneous and solvent-free conditions
Sulfonamides were converted to the corresponding N-acyl sulfonamides with carboxylic acid chlorides and anhydrides in the presence of silica chloride. All reactions were performed in both heterogeneous and solvent-free conditions. This method provides the N-acyl sulfonamides products in good to high yield and purity. Copyright Taylor & Francis Group, LLC.
Massah, Ahmad Reza,Momeni, Ahmad Reza,Dabagh, Mina,Aliyan, Hamid,Naghash, Hamid Javaherian
p. 265 - 273
(2008/03/17)
Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions
Silica sulfuric acid catalyzes efficiently the reaction of sulfonamides with both carboxylic acid anhydrides and chlorides under solvent-free and heterogeneous conditions. All the reactions were done at room temperature and the N-acylsulfonamides were obtained with high yields and purity via an easy work-up procedure. This method is attractive and is in a close agreement with green chemistry. These compounds were also investigated for antibacterial activity, including Gram-positive cocci and Gram-negative bacilli, and carbonic anhydrase II inhibitory activity.
Massah, Ahmad Reza,Adibi, Hadi,Khodarahmi, Reza,Abiri, Ramin,Majnooni, Mohammad Bagher,Shahidi, Sherita,Asadi, Beheshteh,Mehrabi, Masomeh,Zolfigol, Mohammad Ali
p. 5465 - 5472
(2008/12/20)
Aromatic Heteroannulation via Metalation-Cyclization of N-Acyl-2-chlorobenzenesulfonamides and N-Acylbenzenesulfonamides
N-Acyl-2-chlorobenzenesulfonamides 7a-d undergo competitive metal-halogen exchange and ortho-deprotonation or α-deprotonation reactions when treated sequentially with sodium hydride and n-butyllithium.The o-lithio intermediates derived from metal-halogen
Hermann, Christine K. F.,Campbell, James A.,Greenwood, Thomas D.,Lewis, Judith A.,Wolfe, James F.
p. 5328 - 5334
(2007/10/02)
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