145026-07-9Relevant articles and documents
Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates
Kong, Xianqiang,Lin, Long,Chen, Xiaohui,Chen, Yiyi,Wang, Wei,Xu, Bo
, p. 3277 - 3282 (2021/07/26)
Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1′-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.
One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
Zupanc, An?e,Jereb, Marjan
, p. 5991 - 6000 (2021/05/05)
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions
Zhang, Guocai,Tan, Hongsheng,Chen, Weichun,Shen, Hong C.,Lu, Yue,Zheng, Changwu,Xu, Hongxi
, p. 922 - 928 (2020/02/20)
The synthesis of NH-sulfoximines from sulfides has been first developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as the catalyst at room temperature. In this newly developed process, a simple and convenient recycling strategy to regenerate the indispensable hypervalent iodine(III) is used. The resulting 1,2,3-trifluoro-5-iodobezene can be recovered almost quantitively from the mixture by liquid–liquid extraction and then oxidized to give the corresponding iodine(III) species. This optimized procedure is compatible with a broad range of functional groups and can be easily performed on a gram scale, providing a green protocol for the synthesis of sulfoximines.
Sulfoximines-assisted Rh(III)-catalyzed C-H activation and intramolecular annulation for the synthesis of fused isochromeno-1,2-benzothiazines scaffolds under room temperature
Han, Xu,Li, Chunpu,Li, Jian,Liu, Hong,Wang, Bao
, (2020/06/29)
Amild and facile Cp?Rh(III)-catalyzed C-Hactivation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Additionally, retentive configuration of sulfoximides in the conversion has been verified.
Ru (II)-Catalyzed Coupling-Cyclization of Sulfoximines with alpha-Carbonyl Sulfoxonium Ylides as an Approach to 1,2-Benzothiazines
Xie, Haisheng,Lan, Jianyong,Gui, Jiao,Chen, Fengjuan,Jiang, Huangfeng,Zeng, Wei
, p. 3534 - 3543 (2018/08/06)
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.).
NOVEL BIPHENYLSULFOXIMINES AS ALLOSTERIC MODULATORS OF THE DOPAMINE D1 RECEPTOR
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, (2019/01/04)
The present invention relates to new biphenylsulfoximine compounds and, in particular, to their activity as positive allosteric modulators of the dopamine D1 receptor and to their use for the treatment of pathological states for which a stimulator of this receptor activity is indicated. The invention further relates to pharmaceutical compositions containing them and to a process for the preparation of such compounds.
Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information, p. 324 - 327 (2017/12/15)
Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No additional oxidant is needed, and the substrate scope is broad, including a range of heter
Persulfate-promoted oxidative C-N bond coupling of quinoxalinones and: NH -sulfoximines
Sumunnee, Ladawan,Pimpasri, Chaleena,Noikham, Medena,Yotphan, Sirilata
supporting information, p. 2697 - 2704 (2018/04/27)
The persulfate-meditated oxidative C-N bond coupling of the C-H bond of quinoxalinones and the N-H bond of NH-sulfoximines is reported. The reaction proceeds smoothly under transition metal-free conditions and provides good to excellent yields of sulfoximidoyl-functionalized quinoxalinone products under mild conditions. The optimized conditions were found to be suitable for a range of sulfoximine and quinoxalinone substrates. This reaction offers a new and convenient strategy to directly install the sulfoximine moiety into the C3 position of quinoxalinone.
Method for synthesizing sulfoximine compounds from thioether
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Paragraph 0027; 0028, (2017/08/28)
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.
Eaton's reagent-mediated metal-free and efficient synthesis of NH-sulfoximines
Wang, Jianping,Zhang, Jian,Miao, Kun,Yun, Hongying,Shen, Hong C.,Zhao, Weili,Liang, Chungen
supporting information, p. 333 - 337 (2017/01/03)
NH-sulfoximines can be prepared efficiently from corresponding sulfoxides in the presence of sodium azide and Eaton's reagent. This metal-free and efficient methodology is applicable to a wide variety of functionalized sulfoxides to afford NH-sulfoximines in good to excellent yields with shorter reaction time than previously reported methods.
