Aromatic Sulfonyl Chlorides Research Articles

Photoinduced FeCl3-Catalyzed Chlorination of Aromatic Sulfonyl Chloride via Extrusion of SO2 at Room Temperature.

We report, herein, a photoinduced iron-catalyzed direct chlorination of aromatic sulfonyl chloride at room temperature. In this protocol, FeCl3-catalyzed direct chlorination has been realized at room temperature under the irradiation of light (400-410 nm). During the process, many commercially or readily available substituted aromatic sulfonyl chlorides could produce the corresponding aromatic chlorides in moderate to good yields.

Chiral sulfonamides with various N-heterocyclic and aromatic units – Synthesis and antiviral activity evaluation

Chiral sulfonamides with aromatic fragments are important chemical building blocks found widely in many natural products, catalysts, and molecules of biological importance. In this report, we describe the efficient synthesis of a series of chiral sulfonamides which, in addition to the aromatic part (phenyl, biphenyl, and dansyl units), possess N-heterocyclic systems. The described compounds were obtained by nucleophilic substitution of chiral N-heterocyclic amines and commercially available aromatic sulfonyl chlorides under mild conditions. All derivatives were examined in antiviral assay against AdV5, HSV-1, HPIV-3, HCMV, and EMCV viruses.

Water Determination in Aromatic Sulfonyl Chlorides Using the Karl Fischer Titration Method: Scope and Limitations

AbstractThe scope and limitations of the Karl Fischer titration was studied for various aromatic sulfonyl chlorides. Standard addition determination of water content was performed using p‐toluenesulfonyl chloride samples; it was confirmed that the method had high accuracy. A set of substituted aromatic sulfonyl chlorides (95 compounds) was subjected to the Karl Fischer titration in order to establish the relevance of the method depending on the compound structure. It was shown that the method gave satisfactory results and was applicable to most aromatic sulfonyl chlorides, except the compounds possessing strong electron‐withdrawing substituents.

Design, Synthesis, and Characterization of Novel Linomide Analogues and their Evaluation for Anticancer Activity.

According to WHO, in 2017, about 90.5 million people suffered from cancer and about 8.8 million deaths occurred due to disease. Although the chemotherapeutic agents have decreased the mortality among the cancer patients but high toxicity and non-specific targets are still major drawbacks. Many researchers have identified linomide, a 4-hydroxy-2-quinolone derivative, as a lead molecule for the development of anticancer agents. With this background, we thought of the following objective. The objective of this research work involves the synthesis of a series of N-(2-(4- hydroxy-2-oxo-1-phenyl-1,2-dihydroquinolin-3-yl)-2-oxoethyl)-N-alkyl substituted benzene sulfonamides IVa-d (1-3) by replacing the anilide moiety at the third position of linomide with sulfamoylacyl and also N-methyl by N-phenyl functionality. To perform in silico anticancer activity by using Molegro Virtual Docker (MVD-2013, 6.0) software and in vitro anticancer activity by MTT assay. The starting material 4-hydroxy-1-phenylquinolin-2(1H)-one was treated with N-bromosuccinamide to yield compound II. Condensation of compound II with primary amines resulted in compounds IIIa-d, which, on coupling with substituted aromatic sulfonyl chlorides yield the title compounds IVa-d (1-3). All the synthesized compounds were satisfactorily characterized by spectral data. The results of docking revealed that the synthesized compounds exhibited well-conserved hydrogen bonds with one or more amino acid residues in the active pocket of EGFRK tyrosine kinase domain (PDB ID: 1m17). The MolDock Score of compound IVd-1 (-115.503) was the highest amongst those tested. The in vitro anticancer activity results showed that compound IVc-1 (R= - (CH2) 2-CH3 ; R'= -H) and IV d-1 (R= -CH2-C6H5; R'= -H) were found to be most potent against K562 cell line with an IC50 of 0.451 μM/ml and 0.455 μM/ml respectively. Compound IVd-1 also showed better potency against A549 cell line with IC50 value of 0.704 μM/ml. The results of in silico and in vitro anticancer activity are in agreement with each other. Compound IV d-1 was found to be most active of the series.

Arylsulfochlorination of β-aminopropioamidoximes giving 2-aminospiropyrazolylammonium arylsulfonates

The reaction of P-(morpholin-1-yl)propioamidoxime with aromatic sulfonyl chlorides (p-XC6H4SO2Cl; X = CH3O, CH3, H, Br, Cl, NO2) in chloroform in the presence of triethyl-amine does not produce expected O-arylsulfonyl-β-(morpholin-1-yl)propioamidoximes; instead, this reaction affords isomers of the latter compounds, 2-amino-8-oxa-l,5-diazaspiro[4.5]dec-1-ene-5-ammonium arylsulfonates. The structures of the reaction products were established by physicochemical methods, spectroscopy, and X-ray diffraction.

Synthesis, spectral characterization, docking studies and biological activity of urea, thiourea, sulfonamide and carbamate derivatives of imatinib intermediate.

A series of new urea/thiourea derivatives 3a-j were synthesized by simple addition reaction of functionalized phenyl isocyanates/isothiocyanates 2a-j with N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidinamine (imatinib intermediate) (1) in the presence of 1,4-dimethyl piperazine (DMPZ) as a base, and another series of new sulfonamide/carbamate derivatives 5a-k were synthesized by reacting 1 with various substituted aromatic sulfonyl chlorides 4a-f and aromatic/aliphatic chloroformates 4g-k in the presence of DMPZ as a base. The title compounds 3a-j and 5a-k were characterized by IR, 1H, 13C NMR and mass spectral data. Antimicrobial, antioxidant and in silico molecular docking studies were made against aromatase.

Ruthenium-Catalyzed Remote C-H Sulfonylation of N-Aryl-2-aminopyridines with Aromatic Sulfonyl Chlorides.

A ruthenium-catalyzed remote sulfonylation at the C5 position of the pyridine group of N-aryl-2-aminopyridines with aromatic sulfonyl chlorides is described. The mechanistic and deuterium labeling studies clearly reveal that the ruthenametallacycle is a key intermediate in the reaction, which forms via the C-H bond activation. The DFT calculation supports that the C5 position of the 2-aminopyridine group carries a more negative charge (-0.304) as compared with other carbons in the metalacycle intermediate.

ChemInform Abstract: Copper‐Catalyzed Cascade Cyclization of 1,7‐Enynes with Aromatic Sulfonyl Chlorides Toward Selective Assembly of Benzo[j]phenanthridin‐6(5H)‐ones.

AbstractA new method for the cascade cyclization of 1,7‐enynes with aromatic sulfonyl chlorides by using a low‐cost and more abundant Cu catalyst is reported.

Copper-catalyzed cascade cyclization of 1,7-enynes with aromatic sulfonyl chlorides toward selective assembly of benzo[j]phenanthridin-6(5H)-ones.

A step-economical method for the cascade cyclization of 1,7-enynes with aromatic sulfonyl chlorides by using a low-cost and more abundant Cu catalyst is presented. This method allows access to benzo[j]phenanthridin-6(5H)-ones and represents a new Cu-catalyzed cascade cyclization of 1,n-enynes.

ChemInform Abstract: Iron‐Catalyzed Regio‐ and Stereoselective Chlorosulfonylation of Terminal Alkynes with Aromatic Sulfonyl Chlorides.

AbstractThe title reaction allows a new and selective access to (E)‐β‐chlorovinylsulfones.

Iron-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Terminal Alkynes with Aromatic Sulfonyl Chlorides

Terminal alkynes react with aromatic sulfonyl chlorides in the presence of an iron(II) catalyst and a phosphine ligand to give (E)-β-chlorovinylsulfones with 100% regio- and stereoselectivity. Various functional groups, such as chloride, bromide, iodide, nitro, ketone, and aldehyde, are tolerated under the reaction conditions. Addition of tosyl chloride to a 1,6-enyne followed by radical 5-exo-trig cyclization gave an exocyclic alkenylsulfone.

Synthesis of Functionalized 1H-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides

A variety of polysubstituted 1H-indenes can be prepared through the copper-catalyzed arylative cyclization of simple arylalkynes with commercially available aromatic sulfonyl chlorides that function as an aryl group donor. The reaction tolerates a broad range of functional groups, including bromide and iodide, nitrile, ketone, and nitro groups. The reaction allowed the synthesis of polycyclic aromatic hydrocarbons, such as a bis(indene), indacene, and fused polyarene derivatives, some of them showing strong fluorescence in solution and the solid state.

Synthesis of n-methyl-3-carboxy-2-chloro-dibenzo[c,f][1,4,5]oxa-thiazepine s,s-dioxide and its derivatives

A new dibenzo-condensed oxathiazepinecarboxylic acid was obtained starting from the methyl ester of 2,4-dichloro-5-chlorosulfonylbenzoic acid. Derivatives were obtained from N-phenylamide and N-methylamide of 2,4-dichloro-5-chlorosulfonylbenzoic acid. Methods for the preparation of the starting aromatic sulfonyl chlorides were proposed.

Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones

A series of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-dione derivatives 6 (a-d) and 7 (a-g) were synthesized with different substituted aromatic sulfonyl chlorides (R-SO(2)-Cl) and alkyl halides (R-X) and were characterized by (1)H NMR, LC/MS, FTIR and elemental analyses. All the compounds synthesised were evaluated for their cell antiproliferation activity by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The antiproliferative effects of the synthesised compounds were tested against viable human skin fibroblast cell line and carcinoma cell lines namely HeLa cells, HT-29 cells, MCF-7 cells, HepG-2 cells by adopting positive and negative control. The importance of the nitro group on thiazolidinone moiety was confirmed and it was concluded that the fourth position of the substituted aryl ring plays a dominant role and was responsible for the antiproliferative activity. Among the synthesized compounds only 6a, 7e and 7g have potent antiproliferative activity on all the carcinoma cell lines tested.

Direct synthesis of thioethers from sulfonyl chlorides and activated alcohols

An efficient, safe one-pot synthesis of thioethers from aromatic sulfonyl chlorides and activated alcohols has been developed under non-aqueous conditions.

Arylsulfonylation of N-isobutylaniline and its derivatives: experimental study and quantum-chemical calculations

The kinetics of the reactions of benzene-substituted N-isobutylanilines 1a—h with 3-nitrobenzenesulfonyl chloride in propan-2-ol was studied at 298 K. To analyze the reactivities of compounds 1a—h in the arylsulfonylation reactions and substantiate the possible mechanism of these reactions, the geometric, electronic, and energy characteristics of the reagents and a series of model compounds were calculated by the semiempirical quantum-chemical AM1 and PM3 methods. The rate of arylsulfonylation of N-isobutylaniline and its derivatives increases directly proportional to the contributions of the s and p z orbitals of the N atoms to HOMO of amine and of the S atoms to LUMO of sulfonyl chloride. The coefficients of these AOs can be considered as the reactivity indices of the reagents used for arylsulfonylation of substituted N-isobutylanilines with aromatic sulfonyl chlorides. It was proposed that the reaction under study is orbital-controlled.

Organocopper-catalyzed living radical polymerization initiated with aromatic sulfonyl chlorides

The living radical polymerization of methyl methacrylate initiated from aromatic sulfonyl chlorides and catalyzed by the new catalytic systems CuSBu/bpy CuSPh/bpy and CuCCPh/bpy (bpy = 2,2′-bipyridine) is described. For a target degree of polymerization of 200, lowering the ratio of catalyst to sulfonyl chloride group from 1/1 to 0.25/1 mol/mol decreases the values of the experimental rate constant of polymerization from 5.12 × 10−2, 2.4 × 10−2, and 1.87 × 10−2 min−1 to 1.8 × 10−3, 4.9 × 10−3, and 4.2 × 10−3 min−1 for CuSBu, CuSPh, and CuCCPh, respectively, whereas the corresponding initiator efficiency increases from 62 to 99%. The external orders of reaction in the catalyst are 0.79 for CuSPh, 0.88 for CuCCPh, and 1.64 for CuSBu. A mechanistic interpretation that involves the in situ generation of, most likely, the real catalyst CuCl, starting from combinations of CuSBu, CuSPh, and CuCCPh and sulfonyl chloride or alkyl halide growing species, is suggested. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 4353–4361, 2000

A Convenient Synthesis of Sulfones Using Zinc Mediated Coupling Reaction of Sulfonyl Chlorides with Alkyl Halides in Aqueous Media

An efficient procedure for the preparation of sulfones has been developed through a simple reaction of aromatic sulfonyl chlorides with suitable alkyl halides mediated by commercial zinc powder in aqueous media at 0 °C ∼ room temperature.

Indium-mediated Coupling Reaction of Sulfonyl Chlorides with Alkyl Bromides in Water. A Facile Synthesis of Sulfones

Indium-mediated coupling of alkyl bromides with aromatic sulfonyl chlorides gives the corresponding sulfones in aqueous media with moderate to good yields.

ChemInform Abstract: Geminal Azo‐ and Heteroelement Functions. Part 8. Triazolium Salts. Part 2. Derivatives of 4,5‐Dihydro‐5,5‐dimethyl‐1,2,4‐triazol‐3‐one.

AbstractAcylation of 4,5‐dihydro‐5,5‐dimethyl‐1,2,4‐triazol‐3‐one (I) with chloroacetyl chloride (II) or the aromatic sulfonyl chlorides (IV) in the presence of pyridines yields the carboxamide (III) or the sulfonamides (V).