14165-67-4

Usage

Uses

Used in Organic Synthesis:
N-(3,4-Dimethoxyphenethyl)-p-toluenesulfonamide is used as a protecting group for amines and amino acids in organic synthesis. It helps to prevent unwanted reactions, allowing chemists to carry out specific reactions without interference from the amine group.
Used in Pharmaceutical Industry:
N-(3,4-Dimethoxyphenethyl)-p-toluenesulfonamide is used in the pharmaceutical industry for the synthesis of various drugs and medicinal compounds. Its ability to protect amines during chemical synthesis is valuable in the development of new and effective pharmaceuticals.

Upstream product

• 4230-93-7 3,4-dimethoxynitrostyrene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 40173-90-8 3,4-dimethoxyphenethyl bromide 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 56014-50-7 N-(3,4-dimethoxy-phenethyl)-N-(toluene-4-sulfonyl)-glycine 
• 64881-02-3 1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 
• 15937-04-9 5,6-dimethoxy-1-(4′-methylbenzenesulfonyl)indoline 
• 110011-00-2 1,2,3,4-tetrahydro-6,7-dimethoxy-2-[(4-methylphenyl)sulfonyl]-1-(4-nitrophenyl)isoquinoline 
• 23818-68-0 1,2,3,4-tetrahydro-6,7-dimethoxy-2-[(4-methylphenyl)sulfonyl]-1-phenylisoquinoline 
• 64880-98-4 1-isopropyl-6,7-dimethoxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 
• 14165-82-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-[(4-methylphenyl)sulfonyl]isoquinoline 
• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 
• 950676-33-2 tert-butyl (Z)-3-{4,5-dimethoxy-2-[2-(4-methylbenzenesulfonylamino)ethyl]phenyl}prop-2-enyl carbonate 

Relevant academic research and scientific papers

Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: Carbonic anhydrase inhibitory activity and: In silico study

The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF3) adsorbed on molecular sieves (4 ?) as a solid support catalyst for the preparation of sulfon

Cyclometalated Ru(II)-isoquinoline complexes overcome cisplatin resistance of A549/DDP cells by downregulation of Nrf2 via Akt/GSK-3β/Fyn pathway

Both ruthenium (Ru) and isoquinoline (IQ) compounds are regarded as potential anticancer drug candidates. Here, we report the synthesis and characterization of three novel cyclometalated Ru(II)-isoquinoline complexes: RuIQ-3, RuIQ-4, and RuIQ-5, and evalu

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.

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.

Synthesis and cytotoxicity of novel N-sulfonyl-1,2,3,4- tetrahydroisoquinoline thiosemicarbazone derivatives

The modified Pictet-Spengler reaction of phenylethylbenzene sulfonamide with a commercially available glyoxal to construct 1-benzoyl- and 1-acetyl-1,2,3,4-tetrahydroisoquinolines 9a-n has been reported. The reaction could be accomplished, regardless of th

Electron-withdrawing substituted benzenesulfonamides against the predominant community-associated methicillin-resistant Staphylococcus aureus strain USA300

A small focused chemical library constituted of sulfonamides was synthesized. These compounds were designed to lack the p-aminobenzene moiety typically found in sulfonamide antibiotics. Antimicrobial activities of these synthetic compounds were investigated against global predominant methicillin-resistant Staphylococcus aureus (MRSA) strain USA300 (SF8300) and control strains of Staphylococcus aureus (S. aureus) ATCC 25923 and ATCC 29213 using disk diffusion and microdilution assays. Based on susceptibility results, potent S. aureus and MRSA USA300 growth inhibitors such as N-[3,5- bis(trifluoromethyl)phenyl]-4-bromobenzenesulfonamide with minimum inhibitory concentration (MIC) as low as 5.6 μg/cm3 along with other effective sulfonamides were discovered. Structure-activity correlations revealed that these desamino-benzenesulfonamides required electron-withdrawing substituents to be effective inhibitors of bacterial pathogen growth. In addition, their ability to inhibit growth of S. aureus strains was retained even when bacterial folate synthetic intermediate, p-aminobenzoic acid (PABA), was supplemented, whereas PABA supplementation completely diminished the antibacterial activity of the known sulfa drug tested, sulfamethoxazole. The sulfa-resistant MRSA strain COL also showed great susceptibility to these desamino-benzenesulfonamides. These results imply a unique mechanism of growth inhibition by these potent desamino-benzenesulfonamides, different from the well-known folate pathway target of sulfonamide antibiotics.

Synthesis, cytotoxicity and QSAR study of N-tosyl-1,2,3,4- tetrahydroisoquinoline derivatives

1-Substituted-N-tosyl-1,2,3,4-tetrahydroisoquinoline analogs (4a-4l) were synthesized using the modified Pictet-Spengler reaction and evaluated for cytotoxicity. All tetrahydroisoquinolines displayed cytotoxicity against MOLT-3 cell lines, except for p-me

Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives

A new series of benzene and isoquinoline sulfonamide derivatives were synthesized by nucleophilic displacement reaction on benzene and isoquinoline sulfonyl chlorides by substituted amines (primary and secondary). The title compounds were evaluated for an

Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Unde