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Publications (129)
Traditional chemical synthesis, which involves the use of dangerous protocols, hazardous solvents, and toxic products and catalysts, is considered environmentally inappropriate and harmful to human health. Bearing in mind its numerous drawbacks, it has become crucial to substitute conventional chemistry with green chemistry which is safer, more eco...
The objective of this study is to evaluate a series of molecules based on cyclosulfamide as potential anticancer agents. Additionally, the study aims to analyze the obtained results through in silico studies; by conducting experiments and utilizing theoretical methods. In this context, we investigated the cytotoxic activity of enastron analogues on...
New pseudonucleosides containing cyclic sulfamide moiety and sulfamoyl β-D-glucosamine derivative are described. These pseudonucleosides are synthesized in good yields starting from chlorosulfonyl isocyanate and β-D-glucosamine hydrochloride in five steps; (protection, acetylation, removal of the Boc group, sulfamoylation, and cyclization). Further...
In this present study, we describe a simple, effective and greener one-pot microwave-assisted synthesis of novel α-sulfamidophosphonates 4(a–l), and 5(a, b) that were rationally designed and synthesized following the principle of the superposition of bioactives substructures. This reaction was accomplished by the condensation of various aromatic al...
An efficient access to a novel series of organophosphorus compounds with a cyclosulfamide moiety is described. Starting from α-hydroxyphosphonates, the 2-chloroethyl-(1, 2, 5- thiadiazoline-2-carbonyloxy-1- dioxide) phosphonates compounds were prepared in three steps including an abramov reaction, carbamoylation-sulfamoylation with chlorosulfonyl i...
In this present study we describe a simple, effective and greener one-pot microwave-assisted synthesis of novel α-sulfamidophosphonates 4(a-n) that were rationally designed and synthesized following the principle of the superposition of bioactive substructures. This reaction was accomplished by the condensation of various aromatic aldehydes, sulfam...
In this paper, we have developed a new, non-hazardous and eco-friendly access route for the synthesis of a novel Schiff bases containing 2-oxo-3H-benzoxazole scaffold 4(a-f) by lemon juice as natural catalyzed acid under solvent-free conditions. The chemical structures of the new synthesized compounds were elucidated on the basis of the FT-IR, ¹H a...
An eco‐friendly and one‐step microwave‐assisted green synthesis of new functionalized bisphosphonates derivatives was described by a three‐component reaction of aromatic sulfamide with triethyl orthoformate and diethyl phosphite. The synthesized compounds were characterized by 1H, 13C, 31P NMR and IR analysis. Some of these compounds were tested fo...
This review article, containing 52 references, surveys recent achievements of the use of chlorosulfonyl isocyanate (CSI) in organic synthesis. In particular, the application for the preparation of several bioactive products containing the sulfamoyl moiety, which have been published in the last decade, is summarized.
CSI is a versatile reagent and d...
Novel α-aminophosphonates containing 1,2,3-oxathizolidine-2,2-dioxide moiety were described. These molecules were synthesized within two steps starting by the condensation of three compounds (β-amino alcohols, benzaldehyde and triethylphosphite) via Kabachnik-Fields reaction followed by cyclisation with sulfuryl chloride. All products reported in t...
α‐Aminophosphonates play an important role across several fields, including organic synthesis and various potential applications. This review paper surveys recent achievements in the synthesis of α‐Aminophosphonates, it summarizes the main synthetic routes towards α‐Aminophosphonates that are known and it describes their biological proprieties from...
A simple, efficient and eco-friendly protocol has been described for the synthesis of α-aminophosphonates via Kabachnik-Fields reaction, catalyzed by H6P2W18O62·14H2O as a reusable catalyst. The reaction was realized by condensation of amino acids, various aromatic aldehydes and triethylphosphite under solvent-free conditions, the corresponding α-a...
An efficient and eco-friendly process has been developed for the synthesis of _-aminophosphonates containing aminothiazole moiety via Kabachnik-Field reaction catalyzed by H6P2W18O62.14H2O as reusable catalyst, by condensation of aromatic aldehydes, 2-aminothiazole and triethylphosphite under solvent-free conditions. All the newly synthesized compo...
A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.
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 carri...
Correction for ‘A novel, rapid and green method of phosphorylation under ultrasound irradiation and catalyst free conditions’ by Abdeslem Bouzina et al., RSC Adv., 2015, 5, 46272–46275.
An easy and handy synthesis of -sulfamidophosphonates directly by Three-Component reactions is reported. The reaction involves the use of aldehyde, sulfonamides and trimethylphosphite. A wide range of substrates is compatible in this reaction, producing excellent yields in short time. The reaction is performed under solvent- and catalyst-free cond...
An improved environmentally benign method for synthesis of sulfamides under focused ultrasound irradiation and under solvent-free and catalyst-free conditions has been carried out by the reaction of amines or amino esters with sulfuryl chloride. This approach allows the synthesis of products in excellent yields and in short reaction time.
A series of novel N-acylsulfonamide derivatives were synthesized and characterized by
1H NMR, 13C NMR and HRMS. The N-acylsulfonamides were prepared in four steps (carbamoylation,
sulfamoylation, deprotection and acylation) starting from chlorosulfonyl isocyanate. These
compounds were evaluated in vitro as antimicrobial agents against representativ...
In this paper, the structural analysis of two novel derivatives of N-Acylsulfonamides (1a-1b) has been made. Packings of the two crystal structures presented herein are the results of individually weak but synergistic non covalent interactions like typical N-H ... O= (C or S) hydrogen bonds or stacking effects. DFT calculation of molecular elec...
Ultrasound wich is an alternative energy source was investigated for the environmentally benign synthesis of sulfahydantoine (1, 2, 5-thiadiazolidin-3-one S, S-dioxide) starting from different sulfonamides derivatives and bromoacetyl chloride in short reaction time and high yield. These heterocyclic compounds have been characterized by elemental an...
An efficient synthesis of a new series of organophosphorus compounds having a cyclic sulfamidates moiety is described. The cyclic sulfamidate precursors were prepared from α-amino acids after four steps (Reduction, N-Boc protection, cyclisation and cleavage). The novel organophosphonates were synthesized within two steps starting from the cyclic su...
A simple, efficient and environmentally benign method for the synthesis of α-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is effectively accomplished under ultrasound irradiation and solvent-free and catalyst-free conditions. This rapid method produces α-hydroxyphosphonates in high yields and short reaction time...
A convenient method for the synthesis of new series of N-acylsulfonamide containing oxazolidin-2-one moiety starting from chlorosulfonyl isocyanate and chiral oxazolidinones in two steps (carbamoylation and sulfamoylation), is described. The starting oxazolidinones were obtained in two steps starting from amino acids by reduction with NaBH4 then cy...
Previous studies show that the phosphate groups play a role important in the complexation process as a whole more effective donor that carboxylate groups. The presence of the aromatic ring increases the power complexing of these molecules. We present here a spectrophotometric method for the determination of two complex [M(L1)nH2O] L1 = dimethyl (hy...
An efficient protocol was developed for the synthesis of N-sulfonylimines under environment-friendly conditions. Ultrasonic energy was employed to obtain the desired products in excellent yields with high purity under solvent- and catalyst-free conditions. The synthesis of new N-sulfonylimines was accomplished from various N-sulfonamides and benzal...
An efficient, eco-sustainable and greener procedure for the synthesis of α-ureidophosphonates via a one-pot three-component reaction of aldehyde, urea/thiourea and triethylphosphite or diethylphosphite using ultrasonic irradiation under solvent- and catalyst-free conditions at 75°, is developped. The desired products were obtained in excellent yiel...
A new series of N, \(N^{\prime }\)-bis-oxazolidinones-sulfone and 5-chloromethylsulfamoyl-oxazolidin-2-ones have been synthesized in three steps (carbamoylation, sulfamoylation and cyclization) starting from 1,3-dichloroporopan-2-ol, chlorosulfonyl isocyanate and primary or secondary amines. Synthesis has been carried out following simple methodolo...
A rapid and efficient solvent-free one-pot synthesis of novel oxazaphosphinane is described under ultrasound irradiation. This reaction was carried out through a three-component condensation reaction of amino alcohol, aromatic aldehyde, and triethyl phosphite. Ultrasonic effects were established with many advantages, including high yields, shorter...
a new series of sulfonylcycloureas derivatives has been synthesized and evaluated in vitro for their antitumor activity against four cancer cell lines (A431, Jurkat, U266 and K562). These compounds were prepared by the condensation of several sulfonamides (2a-m) with ethyl bis (2-chloroethyl) carbamate (1a).The relative cytotoxicity of these new de...
A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, eff...
A new series of substituted 1, 3, 2-diazaphospholidine-2,5-diones was synthesized by an efficient method, starting
from a primary amines and amino esters. We have established that phenyl phosphonic dichloride is a suitable
reagent allowing the introduction a phosphoryl group. We have prepared the phosphoramidates in two steps. These
compounds provi...
The new methodology offers several advantages such as mild, catalyst-free and solvent-free reaction conditions, short reaction times, good yields, simple work-up procedures and environmental friendliness.
An eco-friendly, simple, mild, chemo selective and highly efficient procedure for the acylation of primary and secondary amine function in various structurally and electronically aliphatic and aromatic compounds affording their corresponding N-Ac derivatives is developed. Mild conditions, simplicity and easier work-up are the main advantages of thi...
The phosphorylation reaction of various N-acylamines, N-acylaminoesters N-acylaminoalcohols and N-acylsulfonamides, with trimethylphosphite or triethylphosphite was effectively promoted under ultrasound irradiation, solvent and catalyst free conditions to produce the corresponding amidophosponate. This rapid method produced the products in short re...
An efficient and convenient one-pot synthesis of novel α-sulfamidophosphonate is described via three-component reaction. This reaction was carried out through a three component condensation reaction of sulfonamide, aromatic aldehyde and triethylphosphite under conventional/ultrasonic techniques, catalyst-free and solvent-free conditions. This metho...
Nitrogen mustards are an extremely active class of alkylating agents that have widespread clinical application in the treatment of various tumors. A series of 1,1-bis(2-chloroethyl)-3-(2-hydroxy ethyl)urea 3(a-c) having different substituent on C-2 have been synthesized from a number of simple and chiral amino alcohols derivatives prepared by reduc...
A rapid and efficient solvent-free one-pot synthesis of novel oxazaphosphinane is described under ultrasound irradiation. This reaction was carried out through a three-component condensation reaction of amino alcohol, aromatic aldehyde, and triethyl phosphite. Ultrasonic effects were established with many advantages, including high yields, shorter...
The reaction of aldehydes with primary sulfonamides under solvent- and catalyst-free conditions is described. This method affords the N-sulfamoyl imines in short reaction times and high yields. Mild conditions, simplicity, inexpensive and easily available reagents, and absence of any auxiliary substances are some other advantages of this procedure.
A convenient synthesis of novel N-N'-substituted 1,2,5-thiadiazolidine 1,1-dioxides starting from amino acids is reported in five step (reduction, carbamoylation-sulfamoylation, intermolecular cyclization via the Mitsunobu reaction and acylation). The newly synthesized compounds were characterized by IR, NMR and mass spectral analysis. Some of the...
Nitrogen mustards are an extremely active class of alkylating agents that have widespread clinical application in the treatment of various tumors.
A Novel series of 1,1-bis(2-chloroethyl)-3-(2-hydroxy ethyl)urea 3(a-c) having different substituent on C-2 have been synthesized from a number of simple and chiral aminoalcools derivatives prepared by r...
The condensation of various sulfonamides with aromatic aldehydes was effectively promoted in the presence of
TBAB to produce the corresponding sulfonylimine products in good yields under solvent-free conditions. The
sulfonamides were prepared starting from chlorosulfonylisocyanate (CSI), primary amine in three steps
(carbamoylation, sulfamoylation...
A series of novel sulfonylureas and N-acylsulfonamides derivatives were synthesized and characterized by 1H NMR, 13C NMR and HRMS. These compounds were synthesized efficiently in two steps (carbamoylation-sulfamoylation), using chlorosulfonyl isocyanate (CSI) that was a suitable reagent for allowing the introduction of a sulfonamide moiety. The ant...
Organic molecules such as tetrathiafulvalene (TTF) and its derivatives are important precursors in the design of new conducting, optical and magnetic materials. A new series of unsymmetrically tetrathiafulvalenes have been synthesised. The synthesis of p-acetoxyphenyl tetrathiafulvalenes 5a-d has been carried out by Wittig reaction and their deprot...
In the present work, a new series of sulfonamide derivatives containing isatin moiety were prepared.
Our synthesis was carried out in two successive steps (acylation and condensation with different sulphonamide
derivatives), using chlorosulfonyl isocyanate and isatin as starting materials. The structure of all compounds
was elucidated by usual spec...
The present study describes a convenient method for the synthesis of new N-acylsulfonamides containing phosphonate moiety. The N-acylsulfonamides were prepared starting from Chlorosulfonyl isocyanate (CSI) in four steps (carbamoylation, sulfamoylation, deprotection and acylation). Trimethylphosphite has been used to introduce the phosphonate moiety...
A series of novel N-acylsulfonamides derivatives were synthesized via direct condensation of parent sulfonamide with ethyl lactate as an acylating agent in the presence of tin (IV) chloride (SnCl4) as a Lewis acid catalyst. The sulfonamides were prepared, starting from chlorosulfonyl isocyanate (CSI), in three steps (carbamoylation, sulfamoylation...
A green and simple approach for the N-Boc protection on structurally diverse amines under ultrasound irradiation is described. Selective N-Boc protection was achieved in excellent isolated yield in a short reaction time at room temperature. Mild conditions, inexpensive and an easily available reagent, and absence of any auxiliary substances are the...
A new simple, efficient, greener, and catalyst-free chemoselective protocol for O-tert-butoxycarbonylation of various structurally hydroxyl compounds was carried out with (Boc)2O under Microwave Irradiation. The corresponding O-tert-butoxycarbonates were obtained in good to excellent yields in short reaction time without any side reactions.
A new environmentally benign, simple, and efficient protocol for the chemoselective sulfonylation of various structurally amines using microwave irradiation under solvent- and catalyst-free conditions is reported. The corresponding sulfonamides were obtained in excellent yields within short reaction times. Simplicity, milder, cleaner and greener co...
A green and simple approach for the N-Boc protection on structurally diverse amines under ultrasound irradiation is described. Selective N-Boc protection was achieved in excellent isolated yield in a short reaction time at room temperature. Mild conditions, inexpensive and an easily available reagent, and absence of any auxiliary substances are the...
A new series of chiral 5-substituted bis-oxazolidinones containing an acylsulfonamide moiety has been
synthesized starting from chlorosulfonyl isocyanate, (L)-ethyl lactate, and oxazolidin-2-ones. All the reactions were conducted at ambient temperature, and the N-acylsulfonamide bis-oxazolidin-2-ones were obtained with high yields within 2 h. Some...
A series of modified acyclic sulfamides and cyclic sulfamides were synthesized efficiently, using sulfuryl chloride that is the suitable available reagent allowing the introduction a sulfamide moiety. The cyclosulfamides were prepared in two steps (duplication and cyclization) starting from a primary amines. These compounds were preliminarily teste...
A greener, efficient, and chemoselective protocol for O-Boc protection/deprotection of a wide range of phenol derivatives is reported under catalyst-free conditions in water-related systems. Unlike previous reports, no additional reagents or catalysts were used, and workup fulfils green chemistry requirements, making the present method even more in...
This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N'-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline were alkylated with benzyl alcohol under Mitsunobu reacti...
A new series of substituted oxazolidin-2-ones containing chloroacetyl and phosphonate groups have been synthesized and their in vitro cytoxicity activities were evaluated against Paramecium sp at different parameters. Their synthesis were easily carried out starting from available oxazolidin-2-ones by chloroacetylation reaction following by introdu...
A series of sulfamides containing two protecting groups have been synthesized starting from N-benzoylaminoacids derivatives of (glycine, alanine, valine, leucine, phenylalanine), chlorosulfonylisocyanate and primary amines. Selective deprotection of the cyclic or linear sulfamides and amines has been achieved by treatment with heteropolyacid, which...
Efficient Deprotection of Boc Group in Sulfamides Using Heteropolyacid Catalyst (HPA)
The synthesis of two new series of functionalized phosphonates is described. A new entry for the synthesis of 5-phosphonoalkyl cyclosulfamides and bis(phosphonoalkyl) sulfamides starting from dihalogeno bis(amino) sulfone has been developed. These compounds have been synthesized in good yields. Triethylphosphite has been used to introduce the phosp...
Phosphorus, Sulfur, and Silicon and the Related Elements Publication details, including instructions for authors and subscription information:page/terms-and-conditions This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic su...
This work was generously supported by the (Direction Generale de la Recherche Scientifique et du Développement Technologique, DGRS-DT), Algerian Ministry of Scientific Research, (FNR), and fruitful discussions with Dr. Malika Ibrahim-Ouali, Université d'Aix Marseille III, France were greatly appreciated Abstract A simple, efficient and eco-friendly...
A simple, efficient, and eco-friendly protocol for the
N
-Boc protection of the amine moiety in a variety of compounds with di-
tert
-butyl dicarbonate under water-acetone catalyst-free conditions is described. The corresponding monocarbamate is obtained in excellent yields on short reaction times. No competitive side reactions such as isocyanate u...
A new synthetic pathway towards pentacyclic steroids was described via a ring-closing metathesis reaction as the key step.
In this work, we described the synthesis of new heterocyclic organophosphorus compounds starting from a primary amine and phenyl phosphonic dichloride (PDCP). The introduction of a phosphoryl group into heterocyclic structures can generate potential chemical and biological activities. We have prepared the phos-phoramidates in only one step. These c...
