10304-39-9

Usage

Uses

Due to the limited information available about 8-(tosylamino)quinoline, its specific applications are not well-documented. However, based on its chemical structure and the presence of a tosyl protecting group, it can be inferred that it may have potential uses in the following areas:
Used in Organic Chemistry:
8-(Tosylamino)quinoline is used as a protecting group for amines, allowing chemists to temporarily make amines less reactive during chemical reactions. This is particularly useful in the synthesis of complex organic molecules where selective reactivity is required.
Used in Pharmaceutical Research:
8-(Tosylamino)quinoline may be used as a starting material or intermediate in the development of new pharmaceutical compounds. Its unique structure and functional groups could potentially be modified to create novel drug candidates with specific therapeutic properties.
Used in Chemical Synthesis:
8-(Tosylamino)quinoline could be employed as a building block or reactant in the synthesis of other organic compounds, particularly those containing quinolines or related structures. Its versatility and the presence of the tosyl protecting group may facilitate the formation of desired products in multi-step synthetic processes.

InChI:InChI=1/C16H14N2O2S/c1-12-7-9-14(10-8-12)21(19,20)18-15-6-2-4-13-5-3-11-17-16(13)15/h2-11,18H,1H3

Upstream product

• 578-66-5 8-amino quinoline 
• 98-59-9 p-toluenesulfonyl chloride 
• 1620100-87-9 8-((4-methylphenyl)sulfonamido)-quinoline N-oxide 
• 88-74-4 2-nitro-aniline 
• 607-35-2 8-nitroquinoline 

Downstream Products

• 56564-15-9 N-allyl-N-quinolin-8-yl-toluene-4-sulfonamide 
• 461054-23-9 Ni(C₉H₆NNSO₂C₆H₄CH₃)2(H₂O)2 
• 16073-27-1 (N-quinolin-8-yl-toluene-4-sulfonamidate)2 Zn complex 
• 1054582-94-3 [(8-(p-tosylamino)quinolinato)AuCl₂] 
• 1337558-54-9 [Pt(PPh₃)2(8-(tosylamino)quinioline(-H))][BPh₄] 

Relevant academic research and scientific papers

Sodium chlorate as a viable substoichiometric oxidant for cobalt-catalyzed oxidative annulation of aryl sulfonamides with alkynes

In this work, NaClO3is demonstrated for the first time as an efficient and versatile oxidant in the catalytic C–H activation reaction. By using sodium chlorate as the oxidant, a highly regioselective cobalt-catalyzed oxidative annulation of ary

Cobalt catalyzed electrochemical [4 + 2] annulation for the synthesis of sultams

Cobalt catalyzed electrochemical [4 + 2] annulation of sulfonamides with alkynes is demonstrated in this work, which provided a practical and environmentally friendly way to synthesize structurally diverse sultams. Notably, by employing anodic oxidation in an undivided cell to recycle the cobalt catalyst, this electrochemical method avoided the utilization of stoichiometric amount of metallic oxidant, delivering H2 as the sole by-product. Moreover, this cobalt catalyzed electrochemical protocol proved to be practical and scalable. When the model reaction was scaled up to 5.0 mmol, 86% yield of product could still be obtained.

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives

We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.

Small molecule SUMOylation activators are novel neuroprotective agents

Neuronal loss characterizes many of the most intractable nervous system diseases that deprive our ageing population of their quality of life. Neuroprotective pharmacological modalities are urgently needed to address this burgeoning population. Small ubiqu

Cobalt-catalyzed aryl C-H activation and highly regioselective intermolecular annulation of sulfonamides with allenes

Herein we describe a cobalt-catalyzed C-H activation of aryl and heteroaryl sulfonamides and their intermolecular heteroannulation reaction with allenes, providing a convergent strategy for the synthesis of biologically interesting heterocyclic scaffolds. Carbometallation of allenes proceeds selectively through a Co-alkenyl pathway for a wide range of electron-poor and electron-rich allenes.

NEUROPROTECTIVE QUINOLINE SULFONAMIDES

Disclosed herein are methods and compositions comprising compounds capable of activating and increasing protein SUMOylation. Disclosed herein are methods and compositions comprising compounds capable of showing neuroprotective and cytoprotective effects w

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

Rhodium(i)-catalyzed mono-selective C-H alkylation of benzenesulfonamides with terminal alkenes

The Rh(i)-catalyzed ortho-alkylation of benzenesulfonamides with alkenes with the aid of an 8-aminoquinoline directing group is reported. The reaction is applicable to a variety of benzenesulfonamide derivatives and various alkenes. Curiously, unactivated

Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow

An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhyda