75391-97-8

Usage

InChI:InChI=1/C13H14N2O2S/c1-11-5-7-13(8-6-11)18(16,17)15-10-12-4-2-3-9-14-12/h2-9,15H,10H2,1H3

Upstream product

• 586-98-1 2-Hydroxymethylpyridine 
• 70-55-3 toluene-4-sulfonamide 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 117053-67-5 N,N-di(2-picolyl)-4-methylbenzenesulfonamide 
• 90719-72-5 N,N'-Ditosyl-6,6'-bis<(2-pyridylmethyl)aminomethyl>-2,2'-bipyridin 
• 90719-78-1 2,6-bis{[(pyrid-2-ylmethyl)(tosyl)amino]methyl}pyridine 
• 502723-66-2 [6-{[(pyrid-2-ylmethyl)(tosyl)amino]methyl}pyrid-2-yl]methanol 
• 873948-86-8 4-amino-3,5-bis{[N-(2-pyridylmethyl)-N-(4-toluenesulfonyl)amino]methyl}-4H-1,2,4-triazole 
• 1539-42-0 bis[(2-pyridyl)methyl]amine 
• 77405-26-6 Ni(C₅H₄NCH₂NSO₂C₆H₄CH₃)2(H₂O)2 
• 353248-11-0 [copper(II)(N-(2-methylpyridyl)toluenesulfonylamidate)2] 
• 475598-57-3 [Co(II)(4-methyl-N-(2-pyridylmethyl)benzenesulfonamide)2(2,2'-bipyridine)] 
• 475598-58-4 [Co(II)(4-methyl-N-(2-pyridylmethyl)benzenesulfonamide)2(1,10-phenanthroline)] 
• 84119-90-4 Co((tosyl)-N-(pyridin-2-ylmethyl)-sulfonamide)₂ 
• 507486-42-2 [Ni(CH₃C₆H₄SO₂NCH₂C₅H₄N)2] 
• 507483-52-5 [Zn(CH₃C₆H₄SO₂NCH₂C₅H₄N)2] 
• 1054582-75-0 [(NC₅H₄CH₂NSO₂C₆H₄CH₃)AuCl₂] 

Relevant academic research and scientific papers

Preparation method of sulfonyl amidine with 2-Picolylamine and DMF-DMA as amine sources

The invention discloses a preparation method of sulfonyl amidine with 2-Picolylamine and DMF-DMA as amine sources. The method comprises the following steps: reacting sulfonyl chloride with 2-Picolylamine to obtain an intermediate product; and then reacting the intermediate product with DMF-DMA in the presence of a catalyst at a temperature of 60-100 DEG C, then performing cooling to room temperature, extracting the reaction solution with ethyl acetate, performing layering, drying and then concentrating to obtain a target product sulfonyl amidine. According to the method disclosed by the invention, the reaction of secondary sulfonamide and DMF-DMA is realized, and the synthesis path of sulfonyl amidine is expanded. The synthetic reaction is simple in operation, mild in condition and convenient in post-treatment, and the obtained intermediate product and the product are high in purity and yield.

Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers

The metal-free, highly selective synthesis of biaryls poses a major challenge in organic synthesis. The scope and mechanism of a promising new approach to (hetero)biaryls by the photochemical fusion of aryl substituents tethered to a traceless sulfonamide linker (photosplicing) are reported. Interrogating photosplicing with varying reaction conditions and comparison of diverse synthetic probes (40 examples, including a suite of heterocycles) showed that the reaction has a surprisingly broad scope and involves neither metals nor radicals. Quantum chemical calculations revealed that the C?C bond is formed by an intramolecular photochemical process that involves an excited singlet state and traversal of a five-membered transition state, and thus consistent ipso–ipso coupling results. These results demonstrate that photosplicing is a unique aryl cross-coupling method in the excited state that can be applied to synthesize a broad range of biaryls.

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

Correlating magnetic anisotropy with the subtle coordination geometry variation of a series of cobalt(ii)-sulfonamide complexes

Systematic substitution on the N-(pyridine-2-ylmethyl)-sulfonamide ligand leads to the subtle variation of the CoN4 coordination geometry in a series of cobalt(ii) complexes sharing the common formula of Co[R1(C6N2/s

One-Pot Synthesis of Sulfonamides from Sodium Sulfinates and Amines via Sulfonyl Bromides

a new and convenient procedure has been developed for the preparation of sulfonamides from sodium sulfinates and amines with (n-C4H9)4NBr as bromine source and m-chloroperbenzoic acid as oxidant. This S-N bond formation reaction proceeds efficiently via sulfonyl bromides under neutral conditions to afford the corresponding sulfonamides in good yields at room temperature.

Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group

The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction.

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.

Phosphine-free thiopseudourea-Pd(II) complex catalyzed Larock heteroannulation of 2-haloamines with internal alkynes

We examined the Pd-catalyzed heteroannulation of 2-haloamines with internal alkynes under phosphinefree conditions. The thiopseudourea palladium(II) complex (5) found to be an efficient catalyst for the Pd induced heteroannulation. Achieved high turnover number for the heteroannulation reactions of internal alkynes with 2-iodoaniline. A variety of 2-bromoanilines and N-tosyl substituted 2-bromoanilines effectively reacted with different substituted internal alkynes to give the corresponding indoles in good to high yields (1:1 ratio of regioisomers).

ARYL-AND HETARYLSULFONAMIDES AS ACTIVE INGREDIENTS AGAINST ABIOTIC PLANT STRESS

Use of substituted sulfonamides of the formula (I) or salts thereof for enhancing stress tolerance in plants to abiotic stress, especially for enhancing plant growth and/or for increasing plant yield.

ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters

Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.