15309-82-7

Usage

InChI:InChI=1/C16H13NO2S/c18-20(19,14-9-2-1-3-10-14)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H

Upstream product

• 127-09-3 sodium acetate 
• 134-32-7 1-amino-naphthalene 
• 98-09-9 benzenesulfonyl chloride 
• 552-46-5 1-naphthylamine hydrochloride 
• 98-10-2 benzenesulfonamide 
• 90-13-1 1-Chloronaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 938-10-3 phenylsulfonyl azide 
• 90-11-9 1-Bromonaphthalene 
• 86-57-7 1-Nitronaphthalene 
• 98-80-6 phenylboronic acid 
• 108-98-5 thiophenol 
• 91-20-3 naphthalene 
• 20474-37-7 benzylsulfonyl azide 

Downstream Products

• 118-44-5 1-N-ethylnaphthylamine 
• 52077-97-1 1-benzenesulfonamido-2,4-dinitronaphthalene 
• 500699-70-7 N-(4-bromo-[1]naphthyl)-benzenesulfonamide 
• 16293-97-3 1-Benzolsulfonyl-N-formylamido-naphthalin 
• 134950-18-8 N-[4,4-Dimethoxy-4H-naphthalen-(1E)-ylidene]-benzenesulfonamide 
• 1338495-69-4 C₂₃H₂₃NO₄S 
• 871901-44-9 N-(4-bromo-2-nitro-[1]naphthyl)-benzenesulfonamide 
• 85218-98-0 1-benzenesulfonamido-2,4-diaminonaphthalene 
• 871901-53-0 N-(1-amino-4-bromo-[2]naphthyl)-benzenesulfonamide 
• 872821-81-3 N-(2-amino-4-bromo-[1]naphthyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Iridium-catalyzed reaction of 1-naphthols, N-(1-naphthyl)benzenesulfonamides, and salicylaldehyde with internal alkynes

1-Naphthols efficiently couple with internal alkynes via cleavage of the C-H bond at the peri-position in the presence of a catalyst system of [IrCl(cod)]2/PBut′3 to selectively afford the corresponding 8-vinyl-1-naphthol derivatives. N-(1-Naphthyl)benzenesulfonamides can similarly react with the alkynes. The reaction of salicylaldehyde with the alkynes using the catalyst system gives 2-hydroxyphenyl vinyl ketones via cleavage of the aldehyde C-H bond.

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

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.

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides

In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system

Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.

Nanocopper-mediated direct arylsulfonamidation of aryl halides with arylsulfonyl azides

An efficient protocol for direct arylsulfonamidation of aryl iodides and aryl bromides using arylsulfonylazides catalyzed by copper nanoparticles is described. Iranian Chemical Society 2012.

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.