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1-Phenyl-3-tosyl-1H-pyrrole was prepared, in moderate yield, by the electrophilic aromatic substitution of 1-phenyl-1H-pyrrole with tosyl chloride in the presence of excess zinc oxide under solvent-free conditions. A minor product was its isomer, 1-phenyl-2-tosyl-1H-pyrrole. [ABSTRACT FROM AUTHOR]

Tosylated 4-aminopyridine and other sulfonylated compounds of amines comprise a substantial class of pharmaceutical drugs used as antibiotics in the field of medicine. This research aimed at the synthesis of tosylated 4-aminopyridine and the complexation of the tosyated 4-aminopyridine with Ni(II) and Fe(II) ions. The sulfonamide was prepared by the action of tosyl chloride on 4-aminopyridine in an aqueous alkaline medium. The complexes were synthesized by the reaction of Ni(NO3)2.6H2O/Fe(NO3)2.6H2O with sulfonamide derivative. These compounds were characterized through Ultraviolet Visible spectroscopy (UV-Vis), Fourier Transform Infer-Red (FTIR) spectroscopy, Proton Nuclear Magnetic Resonance (1HNMR), Carbon-13 Nuclear Magnetic Resonance (13CNMR) and Electron Spray Ionisation-Mass Spectrometer (ESIMS) and micro-analysis. The IR spectral data suggested that the sulfonamide derivative acts as a neutral ligand towards Ni (II) and Fe (II). In their complexes, the coordination frequency bands of 1665.55 and 1674.21 cm-1 were assigned to Ni-N and Fe-N bonds, and 1687.70 cm-1 was assigned to free tosylated 4-aminopyridine. This decrease in the frequency band of free imine to coordinated imine complexes indicates that electron transfer occurred from the ligand to the d-orbitals of the metals. The complexation of4-Methyl-N-(pyridin-4-yl)benzene sulfonamide can increase the biological and catalytic potential of the ligand in the pharmaceutical and chemical industries. [ABSTRACT FROM AUTHOR]

A series of propanamide compounds 6a-l was derived by N-substitution reactions, encompassing tosyl, piperidine and 1,3,4-oxadiazole moieties. The intended array of compounds 6a-l was afforded by a series of five steps reaction scheme. 1-Tosylpiperidin-4-carboxylate (1) was synthesized by the reaction of tosyl chloride (a) with ethyl isonipecotate (b) under mild basic conditions. Compound 1 was subjected to nucleophillic substitution by hydrazine to synthesize 1-tosylpiperidin-4-carbohydrazide (2). The compound, 5-(1-tosylpiperidin-4-yl)-1,3,4-oxadiazole-2-thiol (3) was synthesized by intermolecular cyclization of compound 2 by CS2 under strong basic conditions. The target compounds, 6a-l, were finally synthesized from 3 by reacting with different electrophiles, 5a-l, in an aprotic polar solvent with sodium hydride as an activator. The different propanamoyl electrophiles, 5a-l, were synthesized by the reaction of different aromatic and aliphatic amines, 4a-l, with 3-bromopropionyl chloride under mild basic conditions. The structural elucidation was carried out using modern spectroscopic techniques including IR, 1H-NMR and EI-MS. The antibacterial potential of synthesized compounds was assessed against five bacterial strains. Compounds 6a, 6c, 6d, 6e and 6f were found to be potent antibacterial agents. [ABSTRACT FROM AUTHOR]

In this contribution we demonstrate the feasibility of a recently developed amidation method for a general synthesis of industrially important semi‐synthetic cephalosporin antibiotics starting from readily available 7‐aminocephalosporanic acid and derivatives thereof. The amidation process is based on the use of 4‐toluene‐sulfonyl chloride as an economically attractive coupling reagent in combination with methanol or ethyl acetate as one of the solvent components. A broad reaction scope was shown by the successful synthesis of three further cephalosporin antibiotics with different functionalities, which were obtained in high yields of 82–95 % in the reactions even under non‐optimized conditions. It is noteworthy that also different oxime functionalities in the side chain of the 7′‐position are tolerated as well as an ester moiety in 4′‐position and a cationic functionality in 3′‐position. Thus, this amidation process through an activated anhydride formed by means of 4‐toluenesulfonyl chloride is a broadly applicable methodology for the synthesis of industrial semi‐synthetic cephalosporin antibiotics. [ABSTRACT FROM AUTHOR]

In this study, we have been involved in the synthesis and characterization studies of a new cyclotriorganophosphazenes complex with protected phloroglusine ligand. Firstly,we synthesized hexachlorocyclotirphosphazene from ammonium chloride and phosphorus pentachloride reaction and then two hydroxyl groups of the phloroglusine ligand were protected with methyl iodide and tosyl chloride. Finally, the deprotonated and protected phloroglusine was reacted as an oxygen-containing ligand with hexachlorocyclotriphosphazene in the ratio of 6:1 in THF as a solvent, All of Cl atoms were substituted with hydroxyl groups of ligand to give a new product. This product identified by a series of spectroscopic techniques including FT-IR,31P NMR, 13C NMR, 1H NMR and mass spectrometry

Biogenic amines are group of organic, basic, nitrogenous compounds that naturally occur in plant, microorganism, and animal organisms. Biogenic amines are mainly produced through decarboxylation of amino acids. They are formed during manufacturing of some kind of food and beverages such as cheese, wine, or beer. Histamine, cadaverine, agmatine, tyramine, putrescine, and β-phenylethylamine are the most common biogenic amines found in wines and beers. This group of compounds can be toxic at high concentrations; therefore, their control is very important. Analysis of biogenic amines in alcoholic drinks (beers and wines) was carried out by HPLC-MS/MS after their derivatization with p-toluenesulfonyl chloride (tosyl chloride). The developed method has been applied for analysis of seventeen biogenic amines in twenty-eight samples of lager beers and in twelve samples of different homemade wines (white grape, red grape, strawberry, chokeberry, black currant, plum, apple, raspberry, and quince). The developed method is sensitive and repeatable for majority of the analytes. It is versatile and can be used for the determination of biogenic amines in various alcoholic beverages. Graphical abstract: [ABSTRACT FROM AUTHOR]

An efficient and catalytic α-chlorination of 2-acyl imidazoles with readily available tosyl chloride catalyzed by an octahedral iridium complex under mild condition was reported. A range of 2-acyl imidazoles were converted to their corresponding α-chlorination products in good to excellent yields. [ABSTRACT FROM AUTHOR]

Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.

Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro-polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9-carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including 1H-NMR, 13C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis.

A robust method for preparing (E)- and (Z)-stereodefined fully substituted enol tosylates is described. α-Substituted β-keto esters undergo (E)-selective enol tosylations using TsCl–Me2N(CH2)6NMe2 as the reagent (method A, 13 examples; 63–96%) and (Z)-selective enol tosylations using TsCl–TMEDA–LiCl as the reagent (method B, 13 examples; 62–99%). A plausible mechanism for the (E)- and (Z)-enol tosylation selectivity is proposed. A 1H NMR monitoring experiment revealed that TsCl coupled with TMEDA formed a simple N-sulfonylammonium intermediate. [ABSTRACT FROM AUTHOR]

Various carboxylic acids were converted into N-acylbenzotriazoles (90-97 % isolated yields) via a one-pot synthesis involving activation of carboxylic acids with tosyl chloride. The novel protocol enabled stepwise manipulation of both carboxylic groups of suberic acid en route to Vorinostate (SAHA). In addition to the high yield of SAHA (84% yield over four steps) the new method comprises a simple work up and short reaction times. [ABSTRACT FROM AUTHOR]

Sulfonamides are biologically active compounds with broad spectrum of activities. In the presented research, a small collection of N-alkyl/aralkyl substituted sulfonamides have been synthesized and investigated for inhibition of different bacterial strains. The 1,3-Benzodioxol-5- amine (1) was treated with tosyl chloride (2) in water under mild basic conditions to yield the molecule, N-(1,3-Benzodioxol-5-yl)-4-methylbenzenesulfonamide (3). The target compounds, 5ai, were obtained by stirring 3 with different electrophiles, 4a-i, in the presence of N,N- dimethylformamide and sodium hydride. The structures of the synthesized compounds were established by spectroscopic techniques like IR, 1H-NMR and EI-MS. These compounds were assayed for their antimicrobial activities via screening against Gram-positive and Gram-negative bacteria. The most of the compounds showed moderate activity against P. aeruginosa relative to reference standard drug, ciprofloxacin. [ABSTRACT FROM AUTHOR]

In this article we propose an efficient metal-free method for the mild oxidation of alcohols using dimethyl sulfoxide/tosyl chloride at ambient temperature. The procedure described here is an easy and practical method for the oxidation of primary, secondary, allylic, and benzylic alcohols into their corresponding aldehydes and ketones. The notable advantages of this protocol are mild reaction conditions, good yields and selectivity, and simple workup with minimal waste containing no metallic components. The mechanism of the transformation is also investigated. [ABSTRACT FROM AUTHOR]

Highlights: [•] Synthesis of sulfonamides under mild conditions and ultrasound irradiation. [•] Reaction catalyzed by natural and reusable heterogeneous catalyst. [•] Catalyst can be easily recovered and reused. [•] Better reaction times, higher yields and easier work-up. [•] Side product was not observed under the reaction conditions. [ABSTRACT FROM AUTHOR]

Abstract: A novel series of β-lactams bearing an anthraquinone moiety have been synthesized from imines derived from anthraquinone-2-carbaldehyde and ketenes by a [2+2] cycloaddition reaction. The cycloadducts were fully characterized and evaluated for their antimalarial activities against Plasmodium falciparum K14 resistant strain and showed moderate to excellent EC50 values varying from 9 to 50 μM. [Copyright &y& Elsevier]

Abstract: A simple and efficient procedure for the synthesis of azlactones employing condensation reaction of aromatic aldehydes with hippuric acid has been developed by using the tosyl chloride (TsCl) and dimethylformamide (DMF) system as condensing agent in the absence of solvents under microwave irradiation. The present protocol is operationally simple and offers several advantages such as high yields, short reaction time, and simple workup. [Copyright &y& Elsevier]

Objective: The sole purpose of this study was to synthesize different 4-O-substituted derivatives of N-(4-hydroxyphenyl)-N-methyl-4 methylbenzenesulfonamide and to evaluate their enzyme inhibition activities. Methods: In the present research, a series of O-substituted derivatives of N-(4-hydroxyphenyl)-N-methyl-4-methylbenzenesulfonamide has been synthesized. The parent compound N-(4-hydroxyphenyl)-N-methyl-4-methylbenzenesulfonamide (3) was synthesized by the reaction of metol (planetol or p--methylaminophenol; 1) with tosyl chloride (toluene-4-sulfonyl chloride; 2), which further on treatment with different electrophiles (4, 1 5a-d) in the presence of sodium hydride furnished into 4-O-substituted sulfonamides (6,7a-d). These derivatives were characterized by ¹H-NMR, IR & EI-MS and then screened against 1,1-diphenyl-2-picrylhydrazyl radical (DPPH), acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) enzymes. Results: The screening of the synthesized derivatives showed that these were active against lipoxygenase enzyme and some were remained active against acetylcholinesterase butylcholinesterase enzymes but all were stayed inactive against 1,1-Diphenyl-2-picrylhydrazyl radical. Among these compounds, N-(4-benzoyloxyphenyl)-N-methyl-4-methylbenzene sulfonamide (6) was found to be the most potent inhibitor for lipoxygenase and butylcholinesterase having IC50 value of 57 ± 0.97 and 89 ± 0.79 µmoles relative to quercetin and eserine a reference standards with IC50 value of 37.12 ± 50 50 0.07 and 0.85 ± 0.001 µmoles respectively, probably due to benzoyl group attached to 4-O position of parent molecule 3. Against AChE, N-(4- hydroxyphenyl)-N-methyl-4-methylbenzenesulfonamide (3) itself was found to be the most suitable inhibitor, having IC50 value of 75 ± 0.83 µmoles 50 relative to eserine standard. Conclusion: In all the synthesized compounds, N-(4-benzoyloxyphenyl)-N-methyl-4-methylbenzenesulfonamide (6) was found to be the most potent inhibitor for lipoxygenase and butylcholinesterase enzymes. [ABSTRACT FROM AUTHOR]

Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols. [ABSTRACT FROM AUTHOR]

Excess tosyl chloride used in the tosylation of alcohols is quickly and easily removed by reacting it with cellulosic materials, e.g., filter paper, and filtering. [ABSTRACT FROM AUTHOR]

Abstract: A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted-1,3,4-oxadiazoles in good to very good yields. [ABSTRACT FROM AUTHOR]

The use of polymeric reagents simplifies routine acylation of carboxylic acid because it eliminates the traditional purification. We describe the use of readily available cross-linked poly(4-vinylpyridine) supported tosyl chloride, [P4VP].TsCl, in the suspended solution phase synthesis of symmetrical anhydrides from carboxylic acids in the presence of K2CO3 in high yields and purity. The products can be obtained by filtration and evaporation of the solvent. [ABSTRACT FROM AUTHOR]

A system consisting of tosyl chloride-dimethyl formamide-pyridine was found to ensure oxidation of poly(vinyl alcohol) and some molecular alcohols. [ABSTRACT FROM AUTHOR]

Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiropolycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9- carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including ¹H-NMR, 13C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis. [ABSTRACT FROM AUTHOR]

Abstract: A simple, clean and highly efficient solvent-free procedure for the preparation of primary, secondary, tertiary and aromatic amides is described from the direct reaction of carboxylic acids and silica-supported ammonium salts, triethylamine (TEA) and tosyl chloride (TsCl) as condensing agent. The reaction proceeds rapidly in high yields at room temperature. [Copyright &y& Elsevier]

Immobilization of Aspergillus oryzae β-galactosidase on cotton cloth activated with p-toluenesulfonyl chloride (tosyl chloride) was studied. Enzyme immobilization on the tosylated cotton followed a nucleophilic substitution mechanism as evidenced by UV spectra. NaOH mercerization before tosylation and adding pyridine at a tosyl (g)/pyridine (ml) ratio of 0.2–0.4 increased the final activity of the immobilized enzyme by six-fold. The optimal pH for enzyme immobilization was found to be 4.5. Among different fibrous matrices tested, the knitted cotton cloth showed the highest immobilized enzyme activity. About 50 mg enzyme was immobilized onto each gram of cotton cloth with a protein coupling efficiency of ∼85% and enzyme activity yield of ∼55%. The immobilized enzyme had half-life of ∼50 days at 50 °C, and more than 1 year at 40 °C, an improvement of 25–28-fold as compared to free enzyme. The enzyme immobilized on cotton cloth can be used in a plug-flow reactor for continuous production of galacto-oligosaccharides (GOS) from lactose. The reactor performance was stable, and there was no loss in enzyme activity at 40 °C for the 15-day period studied. The immobilized enzyme also showed same pattern and level of GOS formation from lactose as those from free enzyme reaction, indicating that the reaction kinetics was not affected by immobilization and there was no significant diffusion limitation in the immobilized enzyme reactor. The method to prepare tosylated cotton cloth for enzyme immobilization is simple, inexpensive, and scaleable for industrial applications. Thus, tosylated cotton cloth can be used as a low cost support for highly active and stable biocatalyst. [Copyright &y& Elsevier]

[Figure not available: see fulltext.] A convenient method of accessing imidazole 2-halo derivatives is proposed, comprising O-acylation of imidazole N-oxide fluoroborate complexes with tosyl halogenides which further undergo cine-substitution of 3-tosyl group with a halogen anion. In conjunction with a previously proposed method of synthesizing N-oxides of 2-unsubstituted 1-arylimidazoles this method enables one to substantially expand the range of accessible compounds. [ABSTRACT FROM AUTHOR]

Reactions of hydrochlorides of glycine, alanine, phenylalanine, L-isolcucinc, and L-valine esters with aromatic and heteroaromatic carboxamides afforded hydrochlorides of the corresponding N-(amidomethyl)-α-amino acid esters. N-(Phthalimidomethyl)-α-amino acid esters were obtained by reactions of α-amino acid esters containing free amino groups with formaldehyde and phthalimide, TheH NMR studies demonstrated that the chiral centers of α-amino acids may be retained in the course of condensation. Reactions of the Mannish bases obtained and their hydrochlorides with acetic anhydride and tosyl chloride afforded the corresponding N-aryl and N-sulfonyl derivatives. [ABSTRACT FROM AUTHOR]

A direct method for the synthesis of functional derivatives of N-carboxatnidomethyl- and N-phthalimidomethyl-a-amino acids by the reaction of nitriles and amides of α-amino acids (including peptides) with formaldehyde and NH-compounds (amides and imides) in DMF in the presence of TsOH was developed. The reactions of the compounds synthesized with acetic anhydride, tosyl chloride, and phcnylalanine benzylamide in the presence of dicyclohexylcarbodiimide affording the corresponding N-acyl and N-sulfonyl derivatives or peptides containing carboxamido- and phthalimidomethyl substituents at the terminal N-atom of the peptide chain, were studied. [ABSTRACT FROM AUTHOR]

A facile and odorless one-pot thionation process for the synthesis of N-substituted thioamides using chemically stable and inexpensive thiourea reagent via the Beckmann rearrangement of ketoximes, has been described. [ABSTRACT FROM AUTHOR]