61613-20-5

Usage

Uses

Used in Pharmaceutical Industry:
N-Tosyl-2-iodoaniline is used as a synthetic intermediate for the preparation of spiro-heterocycles, which are considered potential inhibitors of SIRT1. SIRT1 is a protein that plays a crucial role in regulating cellular processes such as metabolism, inflammation, and aging. Inhibition of SIRT1 has been linked to the treatment of various diseases, including cancer, neurodegenerative disorders, and metabolic syndrome. By serving as a key component in the synthesis of these inhibitors, N-Tosyl-2-iodoaniline contributes to the development of novel therapeutic agents targeting SIRT1.
Additionally, N-Tosyl-2-iodoaniline may also find applications in other areas of the pharmaceutical industry, such as the synthesis of other bioactive compounds, drug delivery systems, or as a reagent in various chemical reactions. Its versatility and unique structural features make it a valuable asset in the field of medicinal chemistry and drug discovery.

Upstream product

• 68-34-8 phenyl toluenesulfonamide 
• 1420043-07-7 C₁₅H₁₆INO₂S₂ 
• 62-53-3 aniline 
• 615-43-0 2-iodophenylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 133295-23-5 3-Methylene-2-octyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 133295-22-4 (Z)-20-(Toluene-4-sulfonyl)-20-aza-tricyclo[11.7.0.0^14,19]icosa-12,14⁽¹⁹⁾,15,17-tetraene 
• 127230-11-9 9-N-tosyl-4,4a,9,9a-tetrahydro-3H-carbazole 
• 135190-00-0 2,3-diphenyl-1-(p-toluenesulfonyl)indole 
• 838828-77-6 N-(2-iodo-phenyl)-4-methyl-N-pent-4-enyl-benzenesulfonamide 
• 665033-49-8 N-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Palladium-catalyzed, asymmetric hetero- and carboannulation of allenes using functionally-substituted aryl and vinylic iodides

Aryl and vinylic iodides with a nucleophilic substituent in the ortho or allylic position, respectively, react with 1,2-dienes in the presence of a palladium catalyst and a chiral bisoxazoline ligand to afford five- and six- membered ring heterocycles and carbocycles in good yields and 46-88% enantiomeric excess. The generality of this process has been demonstrated by the use of nucleophilic substituents as varied as tosylamides, alcohols, phenols, carboxylic acids, and stabilized carbanions.

Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles

We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).

Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes

A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Palladium-Catalyzed Chemoselective Oxidative Addition of Allyloxy-Tethered Aryl Iodides: Synthesis of Medium-Sized Rings and Mechanistic Studies

This Letter describes a Pd-catalyzed Tsuji-Trost-type/Heck reaction with allyloxy-tethered aryl iodides and aziridines. The strategy provides efficient access to benzannulated medium-sized rings via intermolecular cyclization. The substrate aryl iodide ha

Efficient and Divergent Synthesis of Medium-Sized Lactams through Zinc-Catalyzed Oxidative Cyclization of Indoly Ynamides?

An efficient zinc-catalyzed oxidative cyclization of readily available indoly ynamides has been developed, enabling rapid and practical access to a diverse array of valuable medium-sized lactams in mostly good to excellent yields with wide substrate scope. In addition, such an asymmetric synthesis has also been explored by employing the chiral substrate.

Deacetylative Aryl Migration of Diaryliodonium Salts with C(sp2)-N Bond Formation toward ortho-Iodo N-Aryl Sulfonamides

An unprecedented approach of metal-free C(sp2)-N bond formation via deacetylation/intramolecular aryl migration is demonstrated with novel N-sulfonamide substituted diaryliodonium salts. The reaction provides a variety of ortho-iodo N-aryl sulf

Gold and Br?nsted Acid Catalyzed Spirocyclization of 2- And 3-Indolyl-Tethered 1,4-Enyne Acetates to Spiro[4, n]alkyl[ b]indoles

A synthetic method to prepare spiro[4,n]alkyl[b]indoles (n = 4-6) efficiently that relies on the gold(I) and Br?nsted acid mediated spirocyclization of 2- and 3-indolyl-tethered 1,4-enyne acetates at room temperature and open to air is described.

Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy

Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of

Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles

A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C-N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C-N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles.