- Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis
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A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C?N bond from the resulting NiIII species at room temperature.
- Liu, Dong,Liu, Zhao-Ran,Ma, Cong,Jiao, Ke-Jin,Sun, Bing,Wei, Lei,Lefranc, Julien,Herbert, Simon,Mei, Tian-Sheng
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supporting information
p. 9444 - 9449
(2021/03/29)
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- Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
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A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.
- Li, Jian,Li, Hui,Fang, Daqing,Liu, Lingjun,Han, Xu,Sun, Jina,Li, Chunpu,Zhou, Yu,Ye, Deju,Liu, Hong
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p. 15217 - 15227
(2021/10/25)
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- Palladium-Catalyzed Oxidative Annulation of Sulfoximines and Arynes by C-H Functionalization as an Approach to Dibenzothiazines
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This work reports a novel and efficient palladium-catalyzed synthesis of tricyclic dibenzothiazines using easily prepared aryl sulfoximines and aryne precursors via C-H functionalization and cyclization. A mechanistic investigation indicated that the C-H bond cleavage at the position ortho to the sulfoximine group is the rate-determining step.
- Li, Jing,Li, Shan,Liu, Liansheng,Wang, Rong,Wei, Junfa,Yang, Yihui
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supporting information
p. 7470 - 7474
(2020/10/09)
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- Ru (II)-Catalyzed Coupling-Cyclization of Sulfoximines with alpha-Carbonyl Sulfoxonium Ylides as an Approach to 1,2-Benzothiazines
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A Ru(II)-catalyzed approach for the rapid assembly of 1,2-benzothiazines has been developed to enable the coupling-cyclization of aryl Csp2?H bonds with α-carbonyl sulfoxonium ylides via Csp2?H activation process. The present method could be further applied to the construction of the 4-substituted 1,2-benzothiazine skeletons. (Figure presented.).
- Xie, Haisheng,Lan, Jianyong,Gui, Jiao,Chen, Fengjuan,Jiang, Huangfeng,Zeng, Wei
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p. 3534 - 3543
(2018/08/06)
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- Method for synthesizing sulfoximine compounds from thioether
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The invention discloses a synthetic method for synthesizing sulfoximine compounds from thioether in one step and application thereof. The synthetic method disclosed by the invention comprises the step of mixing the thioether, an ammonia source and an organic solvent together for carrying out an oxidizing reaction in the presence of an oxidizing agent, thereby obtaining the corresponding sulfoximine compounds. According to the invention, one-step synthesis of the sulfoximine compounds from the thioether is realized for the first time. In recent years, the sulfoximine structure is introduced into the existing drug molecules or high-activity compound molecules, and many high-activity molecules at the clinical stage and listed drug molecules appear. According to the method disclosed by the invention, the drug molecules containing the sulfoximine structure are produced, and the industrial cost can be greatly reduced; and moreover, the synthetic method provided by the invention has the advantages of being high in yield, readily available in raw materials, simple in conditions, simple in reaction equipment, easy in industrialized production, and the like. The structural formula is as shown in the specification.
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Paragraph 0029; 0030
(2017/08/28)
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- Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers
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Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-so
- Tota, Arianna,Zenzola, Marina,Chawner, Stephen J.,John-Campbell, Sahra St,Carlucci, Claudia,Romanazzi, Giuseppe,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
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supporting information
p. 348 - 351
(2017/01/03)
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- Straightforward Strategies for the Preparation of NH-Sulfox-imines: A Serendipitous Story
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Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected 'free' NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches. 1 Introduction 2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts 3 Metal-Free Strategies to Prepare NH-Sulfoximines 4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides 5 Further Applications 6 Conclusion.
- Bull, James A.,Degennaro, Leonardo,Luisi, Renzo
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p. 2525 - 2538
(2017/11/28)
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- Direct: N -acylation of sulfoximines with carboxylic acids catalyzed by the B3NO2 heterocycle
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In contrast to recent significant progress in the development of catalytic methodologies for nitrogen acylations, syntheses of N-acyl sulfoximines have been slow to evolve, and still largely rely on the use of stoichiometric amounts of activating reagents
- Noda, Hidetoshi,Asada, Yasuko,Shibasaki, Masakatsu,Kumagai, Naoya
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supporting information
p. 7447 - 7450
(2017/07/12)
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- Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines
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Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.
- Aithagani, Sravan Kumar,Kumar, Mukesh,Yadav, Mahipal,Vishwakarma, Ram A.,Singh, Parvinder Pal
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p. 5886 - 5894
(2016/07/23)
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- Copper-catalyzed: N -thioetherification of sulfoximines using disulfides
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A novel copper-catalyzed N-thioetherification of sulfoximines under mild reaction conditions was developed. In this procedure, the N-S bond formation was achieved using readily available disulfides as the sulfur source.
- Zhu, Hui,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 11908 - 11911
(2016/10/11)
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- Potent, selective and low-calcemic inhibitors of CYP24 Hydroxylase: 24-Sulfoximine analogues of the hormone 1α,25-dihydroxyvitamin D 3
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A dozen 24-sulfoximine analogues of the hormone 1α,25- dihydroxyvitamin D3 were prepared, differing not only at the stereogenic sulfoximine stereocenter but also at the A-ring. Although these sulfoximines were not active transcriptionally and w
- Kahraman, Mehmet,Sinishtaj, Sandra,Dolan, Patrick M.,Kensler, Thomas W.,Peleg, Sara,Saha, Uttam,Chuang, Samuel S.,Bernstein, Galina,Korczak, Bozena,Posner, Gary H.
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p. 6854 - 6863
(2007/10/03)
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- 24-SULFOXIMINE VITAMIN D3 COMPOUNDS
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The present invention provides novel sulfoximine compounds, compositions comprising these compounds and methods of using these compounds as inhibitors of CYP24. In particular, the compounds of the invention are useful for treating diseases which benefit f
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