69709-34-8

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 612-23-7 2-nitrobenzyl chloride 
• 91718-67-1 (2-nitrobenzyl)(phenyl)sulfane 
• 19169-90-5 bromomethylphenylsulfone 
• 98-95-3 nitrobenzene 
• 7205-98-3 chloromethyl phenyl sulfone 
• 13557-25-0 1-(1-chloroethyl)phenyl sulfone 
• 20808-12-2 fluoromethyl phenyl sulfone 
• 65492-21-9 ((Iodomethyl)sulfonyl)benzene 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 88-73-3 2-Chloronitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 620-88-2 4-nitrophenyl phenyl ether 

Downstream Products

• 790657-30-6 N,N-dimethyl-N-{2-[3-(phenylsulfonyl)-1H-indol-1-yl]ethyl}amine 
• 107266-93-3 N-(2-Benzenesulfonylmethyl-phenyl)-acetimidic acid methyl ester 
• 107267-01-6 2-methyl-3-(phenylsulfonyl)-1H-indole 
• 133437-43-1 3-(phenylsulfonyl)-1H-indole 
• 60986-51-8 2-[2-phenylethenyl]-1H-indole 
• 55968-16-6 2-(2-thienyl)indole 
• 948-65-2 2-phenyl-indole 
• 869301-75-7 N-[2-((1Z,3E)-1-Benzenesulfonyl-4-phenyl-buta-1,3-dienyl)-phenyl]-2,2,2-trifluoro-acetamide 
• 869301-74-6 N-[2-(1-benzenesulfonyl-2-thiophen-2-yl-vinyl)-phenyl]-2,2,2-trifluoro-acetamide 
• 869301-73-5 N-[2-(1-benzenesulfonyl-2-phenyl-vinyl)-phenyl]-2,2,2-trifluoro-acetamide 
• 869301-68-8 N-(2-benzenesulfonylmethyl-phenyl)-2,2,2-trifluoro-acetamide 
• 95539-67-6 2-[(phenylsulfonyl)methyl]aniline 

Relevant academic research and scientific papers

MANUFACTURING METHOD OF COMPOUND HAVING SULFONYL GROUP

The present invention relates to a method for manufacturing a compound having a sulfonyl group, which includes a step for reacting thiosulfonates in a solvent comprising nucleophilic bases with an electrophilic agent. Accordingly, the present invention can manufacture the compound having the sulfonyl group with a variety of structures with high efficiency and high yield through more simplified processes than conventional methods.COPYRIGHT KIPO 2018

Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates

Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.

3-(Arylsulfonyl)-1-(azacyclyl)-1H-indoles are 5-HT6 receptor modulators

Novel 3-(arylsulfonyl)-1-(azacyclyl)-1H-indoles 6 were synthesized as potential 5-HT6 receptor ligands, based on constraining a basic side chain as either a piperidine or a pyrrolidine. Many of these compounds had good 5-HT6 binding affinity with Ki values 50 = 60 nM, Emax = 70%) and antagonists (6y: IC50 = 17 nM, Imax = 86%) were identified in a 5-HT6 adenylyl cyclase assay.

Substituent effects on the electrophilic activity of nitroarenes in reactions with carbanions

The effect on electrophilic activity of substituents located para, ortho, and meta to the nitro group of nitrobenzenes was determined by using vicarious nucleophilic substitution of hydrogen (VNS) with the carbanion of chloromethyl phenyl sulfone (1) as the model process. Values for the relative activities of substituted nitroarenes are given relative to nitrobenzene, which was taken as the standard. This process was chosen as a model reaction because it meets key criteria, such as the wide range of substituents that can be present on the nitrobenzene ring, a low sensitivity to steric hindrance, and in particular the possibility of ensuring conditions in which the overall relative rates of reaction in competitive experiments are equal to the relative rates of nucleophilic addition. The values of relative rates of addition, which were taken to be a measure of electrophilic activity, were determined by competitive experiments in which pairs of nitroarenes competed for the VNS reaction with carbanion of 1. A comprehensive set of data for effects of substituents on the electrophilic activity of nitroarenes is presented for the first time.

Novel synthesis of 2-aryl and 2,3-disubstituted indoles by modified double elimination protocol

(Chemical Equation Presented) Syntheses of 2-aryl and 2,3-substituted indoles were realized by modified double elimination protocol. Under basic conditions, vinyl sulfones derived from the reaction of 2-aminobenzyl sulfone with benzaldehydes underwent cyclization and alkylation followed by elimination of sulfinic acid to afford 2,3-substituted indoles.

Efficient new protocol to synthesize aromatic and heteroaromatic dithioesters

A very efficient, high yielding procedure to synthesize substituted aromatic and heteroaromatic dithioesters is described. It involves the reaction between (phenylsulfonyl)methyl (hetero)aromatic derivatives and elemental sulfur in basic medium, followed by alkylation.

1-Heterocyclylalkyl-3-sulfonyl-indole or -indazole derivatives as 5-hydroxytryptamine-6 ligands

The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the 5-HT6 receptor.

1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands

Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with Ki = 3.7 and 5.7 nM, respectively. Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with Ki = 3.7 and 5.7 nM, respectively.

Synthesis of 4- and 6-substituted nitroindoles

Enolizable ketones react with m-nitroaniline in the presence of strong base such as t-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic σH adducts that are additionally stabilized by intramolecular interaction between the amino and the carbonyl group. Spontaneous oxidation of the σH adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed.

α-(METHYLTHIO)BENZYL SULFONES AS SYNTHETIC INTERMEDIATES. PART IV. SOME NEW o-,m- AND p-SUBSTITUTED α-(METHYLTHIO)- AND α,α'-BIS-(METHYLTHIO)-BENZYL SULFONES

The reaction of the meta nitro, methoxy and cyano substituted benzylic sulfones with an excess of dimethyl disulfide in the presence of NaH/DMSO, affords the corresponding α-monosulfenylated derivatives.However, no reaction occurs with the corresponding o-substituted sulfones.A new procedure is developed using S-methyl methanethiosulfonate, in excess, in the "phase transfer condition" which lead for the o-nitro and o-methoxy substituted sulfones to the α-monosulfenylated derivatives and for the o-cyano as well as p- and m-nitro, m-methoxy and m-cyano substituted benzylic sulfones to the correponding α,α'-bis-sulfenylated derivatives.