A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

Lakrout, Salah; K’tir, Hacène; Amira, Aïcha; Berredjem, Malika; Aouf, Nour‐Eddine

doi:10.1039/c4ra01346h

Cited by 33 publications

(10 citation statements)

References 25 publications

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“…Many catalysts are used for the synthesis of sulfonamides such as, β-Cyclodextrin 27 , water 28,29 , pyridine 30 , PPh 3 31 , DMAP 32 , CsF-Celite 33 , ZnO-nanoparticles 34 , MgO 35 . Lakroutet al, 36 have prepared somesulfonamide derivatives by sulfonylation of primary, secondary sulfonyl chlorides, amino acid esters and phenols under solvent-free microwave irradiation techniques. Pan et al, 28 synthesized a fewsulfonamides via I 2 -mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature.…”

Section: Introductionmentioning

confidence: 99%

Bio-Potent Sulfonamides

Dineshkumar

Thirunarayanan

2019

J. Chil. Chem. Soc.

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Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H 3 PO 3 nano catalyst catalyzed condensation of substituted benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of the sulfonamides are more than 90%. The synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their physical constants, analytical and spectroscopic data. Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby disc diffusion method.

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Section: Introductionmentioning

confidence: 99%

Bio-Potent Sulfonamides

Dineshkumar

Thirunarayanan

2019

J. Chil. Chem. Soc.

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“…Classically substituted sulfonamides may be formed from amines and sulfonyl chlorides, 9 by direct alkylation of sulfonamides with alkyl halides, 10 or through reductive amination. 11 The Mitsunobu reaction has also been employed to convert an alcohol into a sulfonamide.…”

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confidence: 99%

Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions

Wallach

Chisholm

2016

J. Org. Chem.

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An intermolecular alkylation of sulfonamides with trichloroacetimidates is reported. This transformation does not require an exogenous acid, base, or transition metal catalyst, instead the addition occurs in refluxing toluene without additives. The sulfonamide alkylation partner appears to be only limited by sterics, with unsubstituted sulfonamides providing better yields than more encumbered N-alkyl sulfonamides. The trichloroacetimidate alkylating agent must be a stable cation precursor for the substitution reaction to proceed under these conditions. Graphical abstractThe sulfonamide functional group has played an important role in the development of numerous pharmaceuticals. While best known as antibiotics, sulfonamide scaffolds provide a diverse range of biological activity including antitumor, antiviral, diuretic, antiinflammatory and anti-hypertensive properties. 1 Summaries of the top selling pharmaceuticals clearly demonstrate that sulfonamides are well represented in these valuable structures. 2 Data on recently approved pharmaceuticals indicate that sulfonamides continue to be popular in drug discovery, 3 with recent publications in the medicinal chemistry field corroborating that the investigation of sulfonamide-containing structures is ongoing. 4 Sulfonamides also have proven useful in agricultural and insecticidal applications. 5

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“…It was allowed to dry at ambient temperature. The mechanistic design for this reaction was in line with the view of Lakrout et al, [11] Stage1 in the mechanism shown above (Figure 1) depicts the action of tosyl chloride on 2-aminopyridine. The amine group in 2-aminopyridine attacks the sulphonyl group with the pi bond electron between sulphur and oxygen moving to oxygen.…”

Section: Complexation Of Methyl-n-(pyridin-2-yl)benzenementioning

confidence: 55%

“…The important IR spectral bands of the ligand and its metal complexes were given in Table 4. The ligand contains three potential donor sites: the heterocyclic nitrogen of azomethine, the oxygen of sulphonamide and the nitrogen of sulphonamide [11,24,25]. The IR frequency band of the ligand at 3734.13 cm − 1 was assigned to nitrogen of the sulphonamide, the band at 1249.91 cm − 1 was assigned to the sulphonamide oxygen and the band at 1681.98 cm − 1 was assigned to the heterocyclic azomethine nitrogen [19].…”

Section: Electronic Analysis Of Ligand and Complexesmentioning

confidence: 99%

Synthesis and Spectroscopic Studies of Zinc (II) Ion and Copper (II) Ion Complexes of 4-Methyl-<i>N</i>-(pyridin-2-yl)benzene Sulphonamide

Orie¹,

Duru²,

Ngochindo³

2021

WJAC

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Sulphonamide derivative of heteroaromatic compounds has vastly been used as bactericide, fungicide, germicide, antitumor and others in the field of the pharmaceutical industry. Their complexations as revealed by authors are found to enhance the bioactivity of the sulphonamide derivatives except in some cases where bioactive is reduced. 4-methyl-N-(pyridin-2-yl)benzene sulphonamide is an important sulphonamide derivative that houses multiple essential moieties like pyridine core, benzene ring, azomethine and sulphonamide. The synthesis and spectra investigation of Zinc (II) ion and Copper (II) ion complexes of 4-Methyl-N-(pyridin-2-yl)benzene sulphonamide was achieved by two-step reactions. 2-aminopyridine was sulphonylated via the action of tosyl chloride on 4-aminopyridine in the presence of sodium trioxocarbonate (IV) in an aqueous solvent. The product was washed severally with distilled water and purified with mixed solvent. Thereafter, the product was complexed with Zn 2+ and Cu 2+ ions. The purity of both the ligand and complexes were confirmed using thin-layer chromatography and melting point analysis. The solubility analysis confirmed the behaviour of the ligand and the complexes in some organic solvents. The structural elucidations were achieved through Ultraviolet Visible spectroscopy (UV-Vis), Fourier Transform Infer-Red (FTIR) spectroscopy, Proton Nuclear Magnetic Resonance ( 1 HNMR), Carbon-13 Nuclear Magnetic Resonance ( 13 CNMR) and Electron Spray Ionisation-Mass Spectrometer (ESI-MS). The formation of 1:2 [M: 2L] complex was shown in the elemental analysis data. The molar conductance measurements revealed that all the complexes are nonelectrolyte in nature. The infrared (IR) spectra studies indicated the binding sites of the sulphonamide derivatives ligand with the transition metal ions. The spectra of the complexes showed an absorption shift, with the free ligand of azomethine having the absorption band (1681.98) while that of the complexes, Zn (II) and Cu(II) have the absorption bands of 1674.30cm -1 and 1674.27cm -1 respectively. The complexation of4-Methyl-N-(pyridin-2-yl)benzene sulphonamide may hopefully increase the biological and catalytic potential of the ligand in the pharmaceutical and chemical industries.

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A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

Abstract: A new environmentally benign, simple, and efficient protocol for the sulfonylation of amines using microwave irradiation under solvent- & catalyst-free conditions is reported. The corresponding sulfonamides were obtained in excellent yields within short reaction times.

Cited by 33 publications

References 25 publications

Bio-Potent Sulfonamides

Bio-Potent Sulfonamides

Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions

Synthesis and Spectroscopic Studies of Zinc (II) Ion and Copper (II) Ion Complexes of 4-Methyl-<i>N</i>-(pyridin-2-yl)benzene Sulphonamide

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A simple and eco-sustainable method for the sulfonylation of amines under microwave-assisted solvent-free conditions

Abstract: A new environmentally benign, simple, and efficient protocol for the sulfonylation of amines using microwave irradiation under solvent- & catalyst-free conditions is reported. The corresponding sulfonamides were obtained in excellent yields within short reaction times.

Cited by 33 publications

References 25 publications

Bio-Potent Sulfonamides

Bio-Potent Sulfonamides

Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions

Synthesis and Spectroscopic Studies of Zinc (II) Ion and Copper (II) Ion Complexes of 4-Methyl-&lt;i&gt;N&lt;/i&gt;-(pyridin-2-yl)benzene Sulphonamide

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Synthesis and Spectroscopic Studies of Zinc (II) Ion and Copper (II) Ion Complexes of 4-Methyl-<i>N</i>-(pyridin-2-yl)benzene Sulphonamide