95708-23-9

Upstream product

• 106-49-0 p-toluidine 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 16419-60-6 2-Methylphenylboronic acid 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 

Downstream Products

• 93009-22-4 N-Acetyl-N-p-tolyl-p-toluolsulfonamid 
• 680588-95-8 N,N-diethyl-2-[(toluene-2-sulfonyl)-p-tolyl-amino]-acetamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides

The development of Ni-catalyzed C?N cross-couplings of sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only with Pd catalysis, are enabled by use of air-stable (L)NiCl(o-tol) pre-catalysts (L=P

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.

Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes

The copper-mediated fluroalkylation/cyclization of N-allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3-fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low-costing fluoroalkylated sources and excellent functional group tolerance.

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.

Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions

This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole.

N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists

A series of dual OX1R/OX2R orexin antagonists was prepared based on a N-glycine-sulfonamide core. SAR studies of a screening hit led to compounds with low nanomolar affinity for both receptors and good oral bioavailability. One of these compounds, 47, has demonstrated in vivo activity in rats following oral administration.

SULFONYLAMINO-ACETIC ACID DERIVATIVES

The invention relates to novel sulfonylamino-acetic acid derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of such compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.