7230-54-8

Usage

InChI:InChI=1/C10H18NO3/c1-9(2,3)14-8(12)10(4)6-5-7-11(10)13/h7,13H,5-6H2,1-4H3/q+1

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1129-26-6 4-methoxybenzene sulfonamide 
• 93131-73-8 4-tolyl perfluorobutanesulfonate 
• 106-44-5 p-cresol 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 6462-50-6 sodium 4-methoxybenzenesulfinate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 941-55-9 4-toluenesulfonyl azide 
• 106-49-0 p-toluidine 

Downstream Products

• 76410-74-7 4-hydroxy-N-p-tolylbenzenesulfonamide 
• 442865-91-0 C₂₀H₂₆N₂O₄S 
• 432020-17-2 [(4-methoxy-benzenesulfonyl)-p-tolyl-amino]-acetic acid methyl ester 

Relevant academic research and scientific papers

Metal-free synthesis of biaryls from aryl sulfoxides and sulfonanilides via sigmatropic rearrangement

Treatment of aryl sulfoxides and sulfonanilides with trifluoroacetic anhydride resulted in the dehydrative metal-free construction of the corresponding unsymmetrical biaryls. The reaction would proceed via (1) the activation of aryl sulfoxide with the anhydride, (2) interrupted Pummerer reaction of the resulting arylsulfonium with sulfonanilide, (3) [3,3] sigmatropic rearrangement to cleave the transient S–N bond and to form the prospective biaryl C–C bond, and (4) global aromatization. The choice of the amino protecting group is crucial, and only N-sulfonylanilines, i.e., sulfonanilides, could participate in the formation of biaryls.

Sulfonamide compound and metal-free catalytic construction method and application thereof

The invention discloses a sulfonamide compound as shown in a formula (I) which is described in the specification and a synthesis method thereof. A series of sulfonamide compounds are obtained throughreaction of nitroaromatic hydrocarbon, an inorganic sulfur reagent and boric acid as reaction raw materials in a solvent under the action of alkali and an additive. Metal catalysis and an additional reducing agent are not needed, an inorganic sulfur reagent is used as a sulfur source and a reducing agent, and a series of sulfonamide compounds are constructed in one step by a three-component one-pot method. The invention also discloses an application of the sulfonamide compound in synthesis of sulfonamide drugs. The raw materials of the synthesis method are wide in source, cheap and easy to obtain; the reaction operation is simple; the substrate universality is high; and the synthesis method is economic and practical. The sulfonamide compound has high practical value and a wide applicationprospect.

Straightforward Sulfonamidation via Metabisulfite-Mediated Cross Coupling of Nitroarenes and Boronic Acids under Transition-Metal-Free Conditions?

A straightforward multicomponent sulfonamidation of nitroarenes, sodium metabisulfite and boronic acids was established under transition-metal-free conditions to access diverse sulfonamides from readily available and low-cost materials modularly. Inorganic salt sodium metabisulfite not only served as a sulfur dioxide source, but also played a key role for both activator and reductant during sulfonamidation. Notably, naturally occurring biomolecules and pharmaceuticals with multiple heteroatoms and sensitive functional groups were intensively investigated in this transformtion providing versatile sulfonamides collectively. Further mechanistic studies demonstrated that nitrosoarene is the key intermediate, and the activation of boronic acid is the rate-determining step in the transformation.

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

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.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Inhibitors of viral entry into mammalian cells

The present invention is related to the development of compounds and methods for inhibiting viral infection in a mammal. A pseudotype virus was developed for use in a high throughput assay for identifying nonpeptidic small molecule inhibitors that prevent

6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF

The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for

Identification of diarylsulfonamides as agonists of the free fatty acid receptor 4 (FFA4/GPR120)

The exploration of a diarylsulfonamide series of free fatty acid receptor 4 (FFA4/GPR120) agonists is described. This work led to the identification of selective FFA4 agonist 8 (GSK137647A) and selective FFA4 antagonist 39. The in vitro profile of compounds 8 and 39 is presented herein.

Identification of diarylsulfonamides as agonists of the free fatty acid receptor 4 (FFA4/GPR120)

The exploration of a diarylsulfonamide series of free fatty acid receptor 4 (FFA4/GPR120) agonists is described. This work led to the identification of selective FFA4 agonist 8 (GSK137647A) and selective FFA4 antagonist 39. The in vitro profile of compounds 8 and 39 is presented herein.