22865-27-6

Upstream product

• 536-90-3 m-Anisidine 
• 98-09-9 benzenesulfonyl chloride 
• 98-10-2 benzenesulfonamide 
• 2398-37-0 3-methoxyphenyl bromide 
• 938-10-3 phenylsulfonyl azide 

Downstream Products

• 107273-29-0 4-(N-benzenesulfonyl-m-anisidino)-butyric acid 
• 109469-43-4 1-(2-benzenesulfonyl-5-methoxy-phenyl)-pyrrolidin-2-one 
• 613679-11-1 (6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone 
• 56995-13-2 6-methoxy-1-(phenylsulfonyl)-1H-indole 
• 896462-36-5 (1-benzenesulfonyl-6-methoxy-1H-indol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone 
• 896462-49-0 (1-benzenesulfonyl-6-methoxy-1H-indol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanol 
• 896462-56-9 1-benzenesulfonyl-6-methoxy-3-(3,4,5-trimethoxy-benzyl)-1H-indole 
• 99546-93-7 N-(2,2-diethoxyethyl)-N-(3-methoxyphenyl)-benzene-sulfonamide 

Relevant academic research and scientific papers

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation

The Ir-catalyzed mild C-H amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional-group compatibility. Subsequent protodecarboxylation of ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)aniline derivatives, the latter being inaccessible by other C-H functionalization approaches. The decarboxylation step was compatible with the amidation conditions, enabling a convenient one-pot, two-step process. Without a trace: Carboxylic acids are used as traceless directing groups in the Ir-catalyzed direct C-H amidation of arenes with sulfonyl azides under mild conditions. The tandem protodecarboxylation of the ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)anilines, which are difficult to obtain by other C-H functionalization approaches.

Synthesis and biological evaluation of new 3-(6-hydroxyindol-2-yl)-5- (Phenyl) pyridine or pyrazine V-Shaped molecules as kinase inhibitors and cytotoxic agents

We here report the synthesis and biological evaluation of new 3-[(2-indolyl)]-5-phenyl-3,5-pyridine, 3-[(2-indolyl)]-5-phenyl-2,4-pyridine and 3-[(2-indolyl)]-5-phenyl-2,6-pyrazine derivatives designed as potential CDK inhibitors. Indoles and phenyls were

Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3

An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.

Solvent hydrogen bonding and structural effects on nucleophilic aromatic substitution reactions. Part-2: Reaction of benzenesulphonyl chloride with anilines in propan-2-ol/2-methylpropan-2-ol mixtures

Substitution reactions of fourteen para- and meta-substituted anilines with benzenesulphonyl chloride in different mole fractions of propan-2-ol in 2-methylpropan-2-ol have been investigated conductometrically. The second order rate constants correlates satisfactorily with pKa values of the anilines and also with the Hammett's substituent constant. The para-substituted anilines shows a satisfactory correlation with Charton's LDR equation. The results of these correlations indicate the formation of an electron deficient transition state. The rate data correlate satisfactorily with macroscopic solvent parameters such as relative permittivity, εr and polarity, ETN. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters reveals that the solvent dipolarityfpolarizability plays a dominant role in governing the reactivity.

Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents

Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic ana

Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating

The copper-catalyzed N-arylation of sulfonamides with a variety of aryl bromides and iodides using microwave heating is described.

ANALYSIS OF SUBSTITUENT AND SOLVENT EFFECTS ON DISSOCIATION OF N-PHENYLBENZENESULPHONAMIDES

The potentiometric titration in water, methanol, dimethyl sulphoxide, dimethylformamide, and acetonitrile has been used for determination of pK values of 13 N-arylbenzenesulphonamides.The validity of the Hammett and Yukawa-Tsuno models using several sets of substituent constants has been evaluated by the test to check adequacy of the regression function and by the factor analysis.It has been found that the substituent effects in solvents must be interpreted with regard to the experimental method used, solvent, set of the substituent constants, as well as the model equation ETR.The dependence of the Hammett reaction constants on the solvent has been analyzed and reveals a preferred stabilization of the conjugated base through hydrogen bonds.Direct conjugation of the reaction centre with the substituent and with different extent of the solvent-dependence with the 4-CN and 4-NO2 derivatives have been observed.

Kinetische Verfolgung der Sulfamidbildung mittels quantitativer Differentialthermoanalyse

Die Reaktion zwischen Benzolsulfochlorid und einigen Anilinderivaten kann im Bereich oberchalb 200 K mit der dynamischen Technik der DTA untersucht werden, wobei sich eine Reaktion 2.Ordnung ergibt.Aktivierungsparameter und Reaktionsenthalpien werden durch die Anilinsubstituenten beeinflusst.