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

Massah, Ahmad Reza; Asadi, Beheshteh; Hoseinpour, Mahdieh; Molseghi, Azadeh; Kalbasi, Roozbeh Javad; Naghash, Hamid Javaherian

doi:10.1016/j.tet.2009.06.112

Cited by 23 publications

(20 citation statements)

References 33 publications

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“…The use of Lewis acids as catalysts was also explored, giving good yields of products in short times and under mild conditions. [11] ZnO nanoparticles were also used as catalyst in the preparation of N-acylsulfonamides in excellent yields under solvent-free conditions. [11] ZnO nanoparticles were also used as catalyst in the preparation of N-acylsulfonamides in excellent yields under solvent-free conditions.…”

Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

“…[10] Recently, aluminum and zirconium hydrogen sulfates were used as catalysts for the synthesis of N-acylsulfonamides under solvent-free and heterogeneous conditions: high yields of products, short reaction time, and low cost of reagents make attractive this synthetic scheme. [11] ZnO nanoparticles were also used as catalyst in the preparation of N-acylsulfonamides in excellent yields under solvent-free conditions. [12] The use of N-acylbenzotriazoles as acylating agents was described by Katritzky et al: Primary and secondary sulfonamides were acylated in the presence of sodium hydride in 76%-100% yields.…”

Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

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N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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Sulfonamide is a common structural motif in naturally occurring and synthetic medicinal compounds. The rising interest in sulfonamides and N-acyl derivatives is attested by the large number of drugs and lead compounds identified in last years, explored in different fields of medicinal chemistry and showing biological activity. Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors.

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Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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“…The results are reported in (Table 2, entry [5][6][7][8][9][10][11][12][13][14]. In all cases, we obtained the corresponding products N-acyl sulfonamides in good to excellent yields.…”

Section: Resultsmentioning

confidence: 94%

A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation

Bouasla¹,

Bechlem²,

Belhani³

et al. 2017

Orient. J. Chem

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A facile and versatile method for acylation of structurally diverse amines and sulfonamides under focused ultrasonic irradiation in catalyst-free and solvent-free conditions is reported. There are several advantages to this approach such as simple and easier workup conditions, small amount of time and high yielding. The acylation reaction was carried out with acetic anhydride. All structures of synthesized products have been identified by NMR and mass spectroscopy.

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“…In continuation of our research on the acylation reactions [20][21][22][23], we wish to report here the synthesis of a series of new acylating reagents, which are useful for the chemoselective acylation of amino groups of compounds that possess both amino and other groups in water.…”

Section: Introductionmentioning

confidence: 99%

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: highly selective and efficient reagents for acylation of amines in water

Ebrahimi

Saiadi

Dakhilpour

et al. 2015

Zeitschrift Für Naturforschung B

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A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.

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

Cited by 23 publications

References 33 publications

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: highly selective and efficient reagents for acylation of amines in water

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