1143-01-7Relevant articles and documents
Reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with trialkylboranes: Transformation of a boron-carbon bond into a nitrogen-carbon bond
Yang,Dai
, p. 481 - 482 (1993)
N-Toluenesulfonyl protected primary amines were obtained in good to excellent yield by reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with trialkylboranes.
The organocatalytic ring-opening polymerization of: N -tosyl aziridines by an N-heterocyclic carbene
Bakkali-Hassani, Camille,Rieger, Elisabeth,Vignolle, Joan,Wurm, Frederik R.,Carlotti, Stéphane,Taton, Daniel
, p. 9719 - 9722 (2016)
The ring-opening polymerization of N-tosyl aziridines, in the presence of 1,3-bis(isopropyl)-4,5(dimethyl)imidazol-2-ylidene as an organocatalyst and an N-tosyl secondary amine as initiator mimicking the growing chain, provides the first metal-free route
An eco-friendly tandem tosylation/Ferrier N-glycosylation of amines catalyzed by Er(OTf)3 in 2-MeTHF
Nardi, Monica,Cano, Natividad Herrera,De Nino, Antonio,Di Gioia, Maria Luisa,Maiuolo, Loredana,Oliverio, Manuela,Santiago, Ana,Sorrentino, Diletta,Procopio, Antonio
, p. 1721 - 1726 (2017)
Er(OTf)3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-D-glucal and different nucleophiles affording good results in a short time.
Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates
Kornilova, T. A.,Nikitina, D. A.,Zenkevich, I. G.
, p. 1931 - 1941 (2021/09/15)
Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).
Method for synthesizing N-alkyl sulfonamide in water
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Paragraph 0083; 0084; 0085; 0086; 0087, (2020/12/30)
The invention discloses a method for synthesizing N-alkyl sulfonamide in water, in particular to a method for synthesizing an N-alkyl sulfonamide derivative from a sulfonamide derivative and alcohol,and a water-soluble iridium complex is adopted to catalyze the reaction of N-alkyl sulfonamide. Compared with the previous synthesis method, the method has the advantages that a reaction equivalent substrate is used in the reaction process, so that raw material waste is avoided; weak base is used, and reaction conditions are mild; non-toxic and harmless pure water is used as a solvent in the reaction, only water is generated as a by-product, the atom reaction economy is high, and the requirement of green chemistry is met.
The: N -alkylation of sulfonamides with alcohols in water catalyzed by a water-soluble metal-ligand bifunctional iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2
Ai, Yao,Liu, Pengcheng,Liang, Ran,Liu, Yan,Li, Feng
, p. 10755 - 10762 (2019/07/15)
The iridium complex [Cp?Ir(biimH2)(H2O)][OTf]2 (Cp? = η5-pentamethylcyclopentadienyl, biimH2 = 2,2′-biimidazole) was synthesized and developed as a new-type of water-soluble metal-ligand bifunctional catalyst for the N-alkylation of poorly nucleophilic sulfonamides with alcohols in water. In the presence of catalyst (1 mol%) and Cs2CO3 (0.1 equiv.), a series of desirable products was obtained in 74-91% yields under microwave irradiation. Mechanistic experiments revealed that the presence of NH units in the imidazole ligand is crucially important for the catalytic activity of the iridium complex. Notably, this research would facilitate the process of water-soluble metal-ligand bifunctional catalysis for the hydrogen autotransfer process.
A synthetic N-alkyl sulfonamide derivatives
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Paragraph 0103-0106, (2016/10/10)
The invention discloses a method for synthesizing a N-alkyl sulfonamide derivative. The method comprises the following steps: adding a sulfonamide derivative, a water-soluble catalyst, an alkali, alcohol and a solvent into a reaction container; reacting the reaction mixture at 100-120 DEG C for several hours, cooling to room temperature; performing rotary evaporation to remove the solvent, and then separating by a column to obtain the target compound. The method of the invention starts from the sulfonamide derivative, and obtains the N-alkyl sulfonamide derivative through reaction with alcohol. The method of the invention adopts a water-soluble iridium complex as a catalyst; the reaction is carried out in water; and the target compound is obtained with a high yield. Therefore, the reaction meets the requirements for green chemistry, and the method has wide development prospects.
Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-NaI as the Electrolyte Solution at Room Temperature
Zhang, Chen,Chen, Yibin,Yuan, Gaoqing
, p. 1277 - 1282 (2016/12/27)
With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.
A novel rhodium-catalyzed domino-hydroformylation-reaction for the synthesis of sulphonamides
Dong, Kaiwu,Fang, Xianjie,Jackstell, Ralf,Beller, Matthias
supporting information, p. 5059 - 5062 (2015/03/30)
An efficient and highly selective method for the synthesis of sulphonamides by a domino hydroformylation-reductive sulphonamidation reaction has been developed. Various olefins and sulphonamides are converted into the desired products in good yields and with excellent selectivities in the presence of a rhodium/Naphos catalyst. This journal is
Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature
Pan, Xiaojun,Gao, Jian,Liu, Juan,Lai, Junyi,Jiang, Huanfeng,Yuan, Gaoqing
supporting information, p. 1400 - 1403 (2015/03/18)
An efficient I2-mediated approach for the synthesis of sulfonamides at room temperature using water as the solvent has been developed. This method for the synthesis of sulfonamides is quite convenient and environmentally friendly. In addition, the purification procedure of the desired products becomes very easy. This journal is
