15449-00-0

Upstream product

• 128-44-9 saccharin sodium salt 
• 1483-73-4 diphenyliodonium bromide 
• 81-07-2 saccharin 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 62574-72-5 3,3-dichloro-3H-benz[c][1,2]oxathiol 1,1-dioxide 
• 62-53-3 aniline 
• 67-66-3 chloroform 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 34684-21-4 2-chlorosulfonylbenzoyl chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 1131-33-5 2-phenylpyridin N-oxide 
• 19298-36-3 (1,1-dioxo-2-phenyl-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-ylidene)-phenyl-amine 

Downstream Products

• 62-53-3 aniline 
• 174741-00-5 α,α-diphenyl-o-(N-methyl-N-phenylsulfamyl)benzyl alcohol 
• 15448-98-3 3,3-diphenyl-1,2-benzoxathiole 1,1-dioxide 
• 860699-37-2 2-phenylsulfamoyl-benzoic acid 
• 15448-94-9 2-(diphenyl-hydroxy-methyl)-N-phenyl-benzenesulfonamide 

Relevant academic research and scientific papers

Copper-catalyzed arenes amination with saccharins

A novel copper-catalyzed direct C-N formation reaction of simple arenes with cheap and pharmacological saccharin derivatives under relatively mild conditions was developed with arenes as limiting reagents. This work provided a new method for oxidative cou

Promotion of reaction of N-H bonds with triarylbismuth and cupric acetate

Arylation of a diverse group of N-H containing compounds at room temperature with triarylbismuth and cupric acetate in the presence of a tertiary amine promoter, such as triethylamine or pyridine, is described. This mild and highly efficient procedure, which is based on Barton's earlier work on the arylation of amines, can be applied to amides, imides, ureas, carbamates, and sulfonamides. Copyright (C) 1996 Elsevier Science Ltd.

Novel insights on saccharin- and acesulfame-based carbonic anhydrase inhibitors: design, synthesis, modelling investigations and biological activity evaluation

A large library of saccharin and acesulfame derivatives has been synthesised and evaluated against four isoforms of human carbonic anhydrase, the two off-targets hCA I/II and the tumour related isoforms hCA IX/XII. Different strategies of scaffold modification have been attempted on both saccharin as well as acesulfame core leading to the obtainment of 60 compounds. Some of them exhibited inhibitory activity in the nanomolar range, albeit some of the performed changes led to either micromolar activity or to its absence, against hCA IX/XII. Molecular modelling studies focused the attention on the binding mode of these compounds to the enzyme. The proposed inhibition mechanism is the anchoring to zinc-bound water molecule. Docking studies along with molecular dynamics also underlined the importance of the compounds flexibility (e.g. achieved through the insertion of methylene group) which favoured potent and selective hCA inhibition.

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N?O Bond Redox Fragmentation

A simple trifluoromethoxylation method enables non-directed functionalization of C?H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N?O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.

In situ Generation and Utilization of CO: An Efficient Route towards N-Substituted Saccharin via Carbonylative Cyclization of 2-Iodosulfonamides

The present protocol demonstrates the synthesis of N-substituted saccharines via carbonylative cyclization of 2-iodosulfonamides using a Pd(OAc) 2 /Xantphos catalyst system and phenyl formate as a CO source. A variety of saccharin derivatives is synthesized under milder reaction conditions.

Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates

A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.

Preparation method of 2-phenyl-1,1-dioxo-1,2-benzisothiazole-3(2H)-one

The invention relates to a preparation method of 2-phenyl-1,1-dioxo-1,2-benzisothiazole-3(2H)-one. The preparation method comprises the following steps: (1) mixing aniline, water and a fluoboric acid aqueous solution, then dropwise adding a sodium nitrite aqueous solution while stirring at the temperature of 0-5 DEG C, heating to room temperature after dropwise adding is finished, continuing stirring and reacting for 1-2 hours, and carrying out suction filtration to obtain benzenediazonium tetrafluoroborate; (2) stirring and mixing 1,1-dioxo-1,2-benzisothiazole-3(2H)-one, alkali, a copper salt catalyst and a solvent at the temperature from minus 5 DEG C to 5 DEG C, then adding the benzenediazonium tetrafluoroborate in batches, reacting for 6-8 hours while stirring at the temperature from minus 5 DEG C to room temperature, and after reaction is finished, extracting, drying, removing the solvent by evaporation, and carrying out recrystallization to obtain the final product. The copper salt is used as the catalyst, so that reaction time is shortened, and meanwhile, yield is improved; the starting material of the preparation method is easy to obtain, the cost is low, reaction operation is simple, a reaction path is short, industrial production is facilitated, and the application prospect is good.

Decarbonylative C-C bond-forming reactions of saccharins by nickel catalysis: Homocoupling and cycloaddition

Decarbonylation of saccharins by nickel catalysis enables two kinds of C-C bond-forming reactions; homocoupling of saccharins to form biaryls and cycloaddition with alkynes to form benzosultams. The former represents the first reported nickel-catalyzed decarbonylative C-C homocoupling reaction, whereas the latter constitutes a powerful method to pharmaceutically relevant benzosultams. The reactions proceed with good functional-group tolerance and excellent regioselectivity.

Visible-light promoted catalyst-free imidation of arenes and heteroarenes

We described herein a catalyst-free visible-light photolytic protocol for the imidation of arenes and heteroarenes. N-Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo- and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer-proton transfer (ET-PT) is the leading productive pathway for the reaction.

Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation

A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.