7230-41-3

Usage

InChI:InChI=1/C10H11N3O4/c14-10(15)8-2-1-5-12(8)9-4-3-7(6-11-9)13(16)17/h3-4,6,8H,1-2,5H2,(H,14,15)

Upstream product

• 348-54-9 2-Fluoroaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 1493-27-2 ortho-nitrofluorobenzene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 1993-03-9 o-fluorophenylboronic acid 
• 127-65-1 chloroamine-T 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 253602-54-9 (2R)-N-(2-Fluorophenyl)-N-(2-hydroxy-3-benzyloxypropyl)toluene-p-sulfonamide 
• 348-54-9 2-Fluoroaniline 
• 1386995-95-4 N-(2-fluorophenyl)-2-phenyl-N-tosylbutanamide 
• 253602-56-1 2-benzyloxymethyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine 
• 253602-55-0 N-Tosyl-2-phenoxymethyl-1,4-benzoxazine 
• 253602-58-3 2-benzyloxymethyl-3,4-dihydro-2H-benzo[1,4]oxazine 
• 253602-53-8 N-(2-Fluorophenyl)-N-(2-hydroxy-3-phenoxypropyl)toluene-p-sulfonamide 

Relevant academic research and scientific papers

Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium

A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides

A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

Differentiation of isomeric haloanilines by tosylation in combination with electrospray ionization mass spectrometry

Differentiation of the isomeric haloanilines still remains a challenging and?necessary?analytic task due to their identical retention time in chromatography and similar mass spectra. In this work, p-tosylation of haloanilines by reaction of haloanilines with p-toluenesulfonyl chloride resulted in the corresponding N-tosyl haloanilines. Fragmentation of protonated N-tosyl haloanilines in electrospray ionization tandem mass spectrometry (ESI-MS/MS) mainly resulted in tosyl cation, haloaniline radical cation, and halohydroxyaniline radical cation. The MS/MS of the three group isomeric derivatives showed significant difference in abundance distribution of these product ions, respectively. Theoretical calculations showed that the stability of the ion-neutral complex (INC) is a key factor influencing the relative intensity of the product ions. The three group isomeric derivatives were also separated by high performance liquid chromatograph (HPLC) at conventional conditions. p-Tosylation combined tandem MS (or HPLC) technique were carried out to realize the differentiation of isomeric haloanilines.

Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium

A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes

A palladium-catalyzed construction for N-arylsulfonamide from nitroarenes and arylsulfonyl hydrazides is developed. In this protocol, abundant and stable nitroarenes serve as the nitrogen sources by in situ reduction reaction of hydrogen released from arylsulfonyl hydrazides. No external oxidants or reductants are needed for this kind of transformation.

Discovery, Optimization, and Biological Evaluation of Sulfonamidoacetamides as an Inducer of Axon Regeneration

Axon regeneration after injury in the central nervous system is hampered in part because if an age-dependent decline in the intrinsic axon growth potential, and one of the strategies to stimulate axon growth in injured neurons involves pharmacological manipulation of implicated signaling pathways. Here we report phenotypic cell-based screen of chemical libraries and structure-activity-guided optimization that resulted in the identification of compound 7p which promotes neurite outgrowth of cultured primary neurons derived from the hippocampus, cerebral cortex, and retina. In an animal model of optic nerve injury, compound 7p was shown to induce growth of GAP-43 positive axons, indicating that the in vitro neurite outgrowth activity of compound 7p translates into stimulation of axon regeneration in vivo. Further optimization of compound 7p and elucidation of the mechanisms by which it elicits axon regeneration in vivo will provide a rational basis for future efforts to enhance treatment strategies.

Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams

The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.

Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives

Photochemical reaction of variously substituted p-toluenesulfonanilides was studied. The reaction gives rearranged products, o- and p-amino-substituted diaryl sulfones with the combined yields of 38-72%: the p-isomer is more favored over the o-isomer with the selectivity ratio of 1.1-4.3 depending on the substituents. N-Alkylation of the sulfonanilides increases the yields of the rearranged products, and e-withdrawing substituents on the N-phenyl ring does not lower the yields drastically. This study provides simple methodology for the synthesis of o- and p-aminoaryl sulfones which are otherwise not easily accessible.

Studies on development of sufficiently chemoselective N-acylation reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides

A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd.