727-36-6Relevant academic research and scientific papers
Method for synthesizing N-alkyl sulfonamide in water
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Paragraph 0103; 0104; 0105; 0106; 0107, (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.
Method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by boric acid/oxalic acid catalytic system under microwave radiation
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Paragraph 0031; 0076, (2018/09/11)
The invention discloses a method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by a boric acid/oxalic acid catalytic system under microwave radiation. The method includes: adoptingbenzyl alcohol and derivatives thereof and benzene sulfonamide derivatives as raw materials, adopting the boric acid/oxalic acid system as a catalyst, and adopting fluorobenzene as a solvent; performing reaction in a microwave reactor under certain temperature and power conditions, performing vacuum concentration after reaction for a period of time, and subjecting a product to column chromatographic purification to realize efficient catalytic preparation of the N-benzyl benzene sulfonamide compounds. Compared with the prior art, the method has advantages of evidently higher reaction speed than that of conventional heating, mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.
Synthesis process of sulfonamide compounds in microwave system
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Paragraph 0007; 0021; 0026, (2017/08/14)
The invention discloses a synthesis process of sulfonamide compounds in a microwave system. The synthesis process is realized by the following steps: by using CuCl as a catalyst and FeCl3 as an oxidant, carrying out carbon-hydrogen activating and carbon-nitrogen coupling reaction in a DMF (Dimethyl Formamide) by substituting sulfanilamide and methylbenzene through microwave heating and efficient catalysis for 10 to 60 minutes; extracting a product by using ethyl acetate; carrying out vacuum concentration; carrying out column chromatographic purification on a product to obtain the sulfonamide compounds. The synthesis process is a method for efficiently preparing the sulfonamide compounds, which is environment-friendly and is simple and convenient to operate. Compared with the prior art, the synthetic process disclosed by the invention has the advantages of remarkably-increased reaction speed compared with that under a conventional heating condition, mild reaction conditions, simple operation, high yield, safety, low cost and environmental protection.
A synthetic N-alkyl sulfonamide derivatives
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Paragraph 0128-0131, (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.
Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature
Wei, Wei,Liu, Chunli,Yang, Daoshan,Wen, Jiangwei,You, Jinmao,Wang, Hua
supporting information, p. 987 - 992 (2015/03/30)
A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).
The N-alkylation of sulfonamides with alcohols in water catalyzed by the water-soluble iridium complex {Cp*[6,6'-(OH)2bpy](H 2O)}[OTf]2
Qu, Panpan,Sun, Chunlou,Ma, Juan,Li, Feng
, p. 447 - 459 (2014/05/20)
The water-soluble iridium complex {Cp*[6,6'-(OH)2bpy] (H2O)}[OTf]2 (Cp=ν5-pentamethylcyclopentadienyl, bpy=2,2'-bipyridine) was found to be a general and highly efficient catalyst for the Nalkylation of the poor nucleophilic sulfonamides with alcohols as alkylating agents in water. The presence of OH units in the bpy ligand is crucially important for the catalytic activity of the iridium complex. Mechanistic investigations revealed that the catalytically active species is a ligand-metal bifunctional iridium complex bearing an N,N'-chelated 2,2'-bipyridinated ligand and an aqua ligand. Notably, the present catalytic system and the proposed mechanism provide a new horizon and scope for the development of "hydrogen autotransfer (or hydrogen-borrowing) processes".
Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step
Ramunno, Anna,Cosconati, Sandro,Sartini, Stefania,Maglio, Vita,Angiuoli, Sara,La Pietra, Valeria,Di Maro, Salvatore,Giustiniano, Mariateresa,La Motta, Concettina,Da Settimo, Federico,Marinelli, Luciana,Novellino, Ettore
experimental part, p. 216 - 226 (2012/07/16)
Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-α, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase III clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities.
Green and efficient synthesis of sulfonamides catalyzed by nano-Ru/Fe 304
Shi, Feng,Tse, Man Kin,Zhou, Shaolin,Pohl, Marga-Martina,Radnik, Joerg,et al.
supporting information; experimental part, p. 1775 - 1779 (2009/07/25)
The environmentally benign synthesis of carbon-nitrogen bonds continues to be an active and challenging field of chemical research. Here, a novel, environmentally benign method for the direct coupling of sulfonamidesand alcohols is described. Despite the importance of sulfonamide deriva tives as intermediates in drug synthesis, till now such transformations are rarely known. For the first time a domino dehydrogenation-condensation-hydrogenation sequence of alcohols and sulfonamides has been realizedin the presence of a nanostructured catalyst. The magnetic property of the catalyst system allows for convenient isolation of the product and e fficient recycling of the catalyst. A variety of coupling reactions of benzylic alcohols and sulfonamides including various heterocycles were successfully realized, often with >80percent isolated yield. Advantageously, only one equivalent of the primary alcohol is consumed in the process. Mechanistic investigations of the competitive reactions of benzyl alcohol and d7-benzyl alcohol with p-toluenesulfonamide revealed a kinetic isotope effect (kH/kD) of 2.86 (±0.109) for the dehydrogenation of benzyl alcohol and 0.74 (±0.021) for the hydrogenation of N-benzylidene-p-toluenesulfonamide intermediate, which suggests dehydrogenation of the alcohol to be the rate determining step.
