321704-27-2Relevant academic research and scientific papers
Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides
Gillaizeau-Simonian, Nicolas,Barde, Etienne,Guérinot, Amandine,Cossy, Janine
supporting information, p. 4004 - 4008 (2021/02/11)
A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.
2-cyclopropyl-N-benzylbenzenesulfonamide and preparation method thereof
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Paragraph 0010-0013; 0018-0021, (2020/04/17)
The invention discloses 2-cyclopropyl-N-benzylbenzenesulfonamide and a preparation method thereof. The preparation method comprises the following steps: dissolving 2-bromobenzenesulfonic acid and benzylamine in pyridine, then adding a condensing agent EDC-HCl into the solution, carrying out a reaction process at a temperature of 50 to 80 DEG C for 2 to 3h so as to obtain 2-bromo-N-benzylbenzenesulfonamide, dissolving the 2-bromo-N-benzylbenzenesulfonamide in a dioxane solution, then adding cyclopropylboronic acid, sodium carbonate, water and Pd(dppf)Cl2 into the solution, carrying out a reaction process on the mixed system at 110 DEG C in a nitrogen atmosphere for 8-10 hours, and carrying out aftertreatment to obtain 2-cyclopropyl-N-benzylbenzenesulfonamide. The synthetic route disclosed by the invention is short, and only two-step reaction is adopted. The preparation method is strong in operability and high in yield and is an excellent method suitable for large-scale preparation. Because the compounds are valuable drug intermediates, the disclosed content has important research and practical values.
Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis
Tao, Ye,Gilbertson, Scott R.
supporting information, p. 11292 - 11295 (2018/10/26)
The bis(trifluoromethane)sulfonimide (Tf2NH) catalyzed intramolecular hydroamidation of terminal alkynes is reported. The combination of Et3SiH and Tf2NH provides cis-1,3-disubstituted isoindolines and sultams in high yield (up to 98%) and high diastereoselectivity (up to 99?:?1 d.r.).
Regio- and Stereoselective Synthesis of Benzo-δ-sultams by Palladium-Catalyzed Hydrocarbonation of Alkynes
Debnath, Sudarshan,Mondal, Shovan
, p. 710 - 722 (2016/03/01)
An efficient method for the synthesis of benzo-δ-sultams [(4Z)-4-benzylidene-2-(arylmethyl)-3,4-dihydro-2H-1,2-benzothiazine 1,1-dioxides] via palladium(0)-catalyzed hydrocarbonation of alkynes is presented. This method allows regioselective access to a variety of substituted benzosultams in excellent yields under mild conditions. The stereochemistry of the exocyclic double bond of the benzosultam derivatives is confirmed by single-crystal X-ray diffraction.
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%).
Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s
Sun, Lang,Zhu, Yuanxun,Wang, Jing,Lu, Ping,Wang, Yanguang
supporting information, p. 242 - 245 (2015/02/19)
A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.
Benzonitrile oxide cycloadditions with exocyclic methylene benzothiazepine dioxides
Ryan, Sarah J.,Francis, Craig L.,Savage, G. Paul
, p. 381 - 388 (2014/04/03)
N-substituted 5-methylene-2,3,4,5-tetrahydrobenzo[f][1,2]thiazepine 1,1-dioxides underwent 1,3-dipolar cycloaddition with benzonitrile oxide, generated in situ, to give isoxazoline spiro adducts. The cycloadditions were completely regioselective to give the hitherto unreported 3,4-dihydro-2H, 4′ H-spiro[benzo[f][1,2]thiazepine-5, 5′-isoxazole] 1,1-dioxide cycloadduct. Where the N-substituent on the sulfonamide cycloaddition precursor was a 2-substituted arene, the resulting atropisomerism along the N-aryl bond led to facial selectivity in the cycloaddition reaction, with greater than 90% diastereoselectivity. CSIRO 2014.
Palladium-catalyzed C-C coupling of aryl halides with isocyanides: An alternative method for the stereoselective synthesis of (3E)-(Imino)isoindolin- 1-ones and (3E)-(imino)thiaisoindoline 1,1-dioxides
Liu, Bifu,Li, Yibiao,Jiang, Huanfeng,Yin, Meizhou,Huang, Huawen
, p. 2288 - 2300 (2012/11/07)
A palladium-catalyzed, one-pot cyclization reaction to construct (3E)-(imino)isoindolin-1-ones and (3E)-(imino)thiaisoindoline 1,1-dioxides by introducing ortho-reactive functional groups on aryl halides is reported. Under optimal conditions, the cyclization reaction afforded the corresponding products in good to excellent yields (up to 93%) with high stereoselectivity. Notably, this transformation successfully extends its application for the synthesis of phenanthridines and dibenzooxazepines. This new synthetic protocol not only extends the application platform for palladium-catalyzed C-C coupling of aryl halides with isocyanides, but also opens atom-economic and step-economic synthetic routes for nitrogen-containing heterocyclic compounds with wide functional group compatibility. Copyright
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.
α-Haloarylsulfonamides: multiple cyclization pathways to skeletally diverse benzofused sultams
Rayabarapu, Dinesh Kumar,Zhou, Aihua,Jeon, Kyu Ok,Samarakoon, Thiwanka,Rolfe, Alan,Siddiqui, Hina,Hanson, Paul R.
experimental part, p. 3180 - 3188 (2009/08/15)
The development of new methods to skeletally diverse sultams based on a central α-halo benzene sulfonamide building block is reported. Several salient features of this building block are utilized in multiple reaction pathways, including the Heck reaction, C- and O-arylation, Sonogashira-Pauson-Khand, Sonogashira-intramolecular hydroamination, and domino aza-Michael-Heck for the generation of five-, six-, and seven-membered benzofused bicyclic and tricyclic sultams.
