A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts

被引：28

作者：

Massah, Ahmad Reza ^{[1
,2
]}

Asadi, Beheshteh ^{[1
]}

Hoseinpour, Mahdieh ^{[1
]}

Molseghi, Azadeh ^{[1
]}

Kalbasi, Roozbeh Javad ^{[2
]}

Naghash, Hamid Javaherian ^{[2
]}

机构：

[1] Islamic Azad Univ, Dept Chem, Shahreza Branch, Esfahan, Iran

[2] Islamic Azad Univ, Razi Chem Res Ctr, Shahreza Branch, Esfahan, Iran

来源：

TETRAHEDRON | 2009年 / 65卷 / 36期

关键词：

N-Acylation; N-Acylsulfonamide; Aluminum hydrogen sulfate; Zirconium hydrogen sulfate; Solvent-free reactions; Heterogeneous catalysis; RECEPTOR ANTAGONISTS; CARBONYL-COMPOUNDS; ACID; MILD; SULFONAMIDES; ACYLATION; CONVENIENT; REAGENTS; AFFINITY;

D O I：

10.1016/j.tet.2009.06.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7696 / 7705

页数：10

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