63113-47-3

Upstream product

• 3076-56-0 p-tolyllead triacetate 
• 128-44-9 saccharin sodium salt 
• 106-49-0 p-toluidine 
• 26638-43-7 2-methoxycarbonylbenzenesulfonyl chloride 
• 5720-05-8 4-methylphenylboronic acid 
• 81-07-2 saccharin 
• 81-08-3 2-sulfobenzoic acid cyclic anhydride 
• 35812-01-2 N-bromosaccharin 
• 108-88-3 toluene 
• 111887-00-4 2-p-tolylsulfamoyl-benzoic acid 
• 1864-94-4 phenyl formate 

Downstream Products

• 88312-76-9 3-butyl-3-methoxy-2-(4-methylphenyl)-2,3-dihydro-1,2-benzisothiazol 1,1-dioxide 
• 111887-00-4 2-p-tolylsulfamoyl-benzoic acid 

Relevant academic research and scientific papers

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.

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.

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.

BENZISOTHIAZOLINE DERIVATIVE, PLANT DISEASE CONTROL AGENT FOR AGRICULTURAL OR HORTICULTURAL USE, AND PEST CONTROL AGENT FOR AGRICULTURAL OR HORTICULTURAL USE

A plant disease control agent for agricultural or horticultural use and a pest control agent for agricultural or horticultural use, which contain a benzisothiazoline derivative or a salt thereof as an active ingredient and have the following marked effect

Copper-catalyzed general C-N and C-O bond cross-coupling with arylboronic acid

General catalytic Cu(OAc)2/TEMPO in air or Cu(OAc)2/O2 systems for the C-N and C-O cross-coupling reactions with arylboronic acid have been discovered. N- and O-vinylation have also been demonstrated.

New N- and O-arylations with phenylboronic acids and cupric acetate

A new method of arylating N-H and O-H containing compounds at room temperature with phenylboronic acids and cupric acetate in the presence of a tertiary amine promoter is described. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.

New synthetic applications of aryllead triacetates. N-arylation of amides

p-Tolyllead triacetate efficiently arylates the nitrogen atom of carboxamide, sulfonamide, imide, and hydantoin anions under mild conditions. This reaction did not interfere with the arylation of amino and β-dicarbonyl groups.

Amide N-Arylation with p-Tolyllead Triacetate

The N-arylation of several types of amidic nitrogen atoms, including those found in carboxamides, sulfonamides, carboxylic acid imides, mixed carboxylic-sulfonic imides and hydantoin systems was carried out by treatment of their sodium salts with p-tolyllead triacetate in the presence of copper(II) acetate.

HETEROCYCLIC SYNTHESES VIA CARBANIONICALLY INDUCED REARRANGEMENT REACTIONS

The easily occuring -migrations of sulfonyl and carbonyl functions to neighboring phenyl anions can be utilized for ring expansions by one benzo unit when suitably tailored precursor heterocycles are used.Thus, the 1,2- benzisothiazol dioxide systems 8 and 17 can be transformed into dibenzothiazepin dioxides 12 and 21, respectively, whereas the dibenzo- and 1,2,4-benzothiazin dioxide models 35 and 46 give rise to the tribenzothiazocin dioxide and dibenzothiadiazocin dioxide systems 38 and 47, respectively.Unexpected formations of heterocyclic systems, namely, spirobenzoxazin-5,1'(3H)-isobenzofuran> 55, 3,1-benzoxazin 62, and phenanthridinium-salt 70 took place when phtalimide 52, dibenzoylaniline 56, and biphenylylbenzamide 65 were reacted with t-BuLi.