An Eco-friendly and Highly Efficient route for N-acylation under Catalyst-free Conditions

Ouarna, Souad; K’tir, Hacène; Lakrout, Salah; Ghorab, Hamida; Amira, Aïcha; Aouf, Zineb; Berredjem, Malika; Aouf, Nour

doi:10.13005/ojc/310235

Cited by 8 publications

(5 citation statements)

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“…Following our efforts to develop novel methods for acylation [24][25][26][27]12 and in continuation of our investigation on the use of ultrasound irradiation to accelerate reactions [28][29][30] , we describe a novel method for acylation the different amines and sulfonamides with acetic anhydride under ultrasonic irradiation, in absence of solvent and catalyst.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

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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“…An eco-friendly and highly efficient procedure for the Nacylation of sulfonamides under catalyst-free conditions was reported in 2015 by Ouarna et al. [53] The sulfonamide (119) were traded with acetic anhydride (120) as an acylating agent in the water or solvent-free, in the absence of any catalyst. The reaction was complete in 8 minutes and expected product (121) was obtained in 92 % (Scheme 22).…”

Section: Synthesis Of N-acylsulfonamidesmentioning

confidence: 99%

“…the synthesis of various sulfonamide amino acid (53) and (54). The preparation of N-sulfonylformamidines is reported via the direct condensation of sulfonyl chlorides (50) with p-hydroxybenzoic acid (52) or amino acids (51) in water with Na 2 CO 3 .…”

Section: Conflict Of Interestsmentioning

confidence: 99%

Recent Progress in Synthesis of Sulfonamides and N‐Acylsulfonamides, Biological Applications and Their Structure‐Activity Relationship (SAR) Studies

Berredjem,

Bouchareb,

Djouad

et al. 2023

ChemistrySelect

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In recent years, sulfonamide and N‐acylsulfonamide have emerged as prominent areas of scientific research across multiple fields, including chemistry, biology, and medicine. The large number of drugs and lead compounds reported in recent literature evidences the growing interest in these derivatives. Chemists are increasingly intrigued by these molecules owing to their seemingly limitless potential to serve as preferred molecules for numerous applications. Consequently, powerful activities are needed to think of new efficacious therapeutic agents, and it is imperative to discover novel synthetic analogs towards bacterial targets. Advancements in medicinal chemistry have focused on the development of novel sulfonamide and NAS‐bearing analogs that are less harmful, exhibit minimum side‐effort and enhanced dynamic properties. These advanced research areas are currently at the forefront of scientific inquiry. This present review elucidates the contemporary advancements in sulfonamide and N‐acylsulfonamide derivatives, which exhibit diverse and promising pharmacological activities. The different aspects of structure‐activity relationship (SAR) were discussed.

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“…Despite the ubiquitous nature of this functional group, there has not been any report on the direct amidation without prior activation of the carbonyl functional group. Almost all known synthetic routes use catalysts and other means of activation to enable the formation of the amide bond. − In particular, acetamides have many applications and are important to the polymer, agrochemical, and pharmaceutical industries. − Not surprisingly, these have been traditionally synthesized through the reaction of activated acylating agents (e.g., acetic anhydride and acetyl chloride) with amines. However, the toxicity and hygroscopic nature of acetic anhydride and acetyl chloride make them less favorable as acylating agents .…”

Section: Introductionmentioning

confidence: 99%

Monoacylation of Symmetrical Diamines in Charge Microdroplets

Ansu-Gyeabourh

Amoah

Ganesa

et al. 2020

J. Am. Soc. Mass Spectrom.

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Monoacylation of symmetrical diamine is achieved when the primary α,ω-diamines (carbon numbers n = 3, 5 and 12) are diluted in ethyl acetate, and the resultant mixture is electrosprayed across a 10 mm distance in ambient air toward a mass spectrometer. The N-acylated product is formed in charged microdroplets without acidifying and activating agents and in the absence of heat. This result provided an insight into the orientation of the amines in the droplets, suggesting that the ester is activated to react with the amine at the droplet surface due to the high abundance of protons at the air−droplet interface.

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An Eco-friendly and Highly Efficient route for N-acylation under Catalyst-free Conditions

Cited by 8 publications

References 0 publications

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

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

Recent Progress in Synthesis of Sulfonamides and N‐Acylsulfonamides, Biological Applications and Their Structure‐Activity Relationship (SAR) Studies

Monoacylation of Symmetrical Diamines in Charge Microdroplets

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