- One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
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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.
- Zupanc, An?e,Jereb, Marjan
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p. 5991 - 6000
(2021/05/05)
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- 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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- BIARYL DERIVATIVE, PREPARATION METHOD THEREOF AND PHARMACEUTICAL APPLICATION THEREOF
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Disclosed are a biaryl derivative having a structure represented by Formula (I) and inhibitory activity against PD-1/PD-L1 interaction, a preparation method thereof, and a pharmaceutical application thereof. The series of compounds of the present inventio
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Paragraph 0099; 0140; 0141
(2020/12/22)
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- HETEROCYCLIC INHIBITORS OF ATR KINASE
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The present disclosure relates to heterocyclic compounds and methods which inhibit ATR kinase to treat or prevent cancer.
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- I2/PhI(OAc)2 Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide
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An I2/PhI(OAc)2 copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing α-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amin
- Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Zhou, You,Wu, Yan-Dong,Wu, An-Xin
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supporting information
p. 8322 - 8329
(2019/06/27)
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- HETEROCYCLIC INHIBITORS OF ATR KINASE
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The present disclosure relates to heterocyclic compounds and methods which may be useful as inhibitors of ATR kinase for the treatment or prevention of cancer.
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Paragraph 0656; 0660-0661
(2019/02/01)
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- SULFOXIMINE, SULFONIMIDAMIDE, SULFONDIIMINE AND DIIMIDOSULFONAMIDE COMPOUNDS AS INHIBITORS OF INDOLEAMINE 2, 3-DIOXYGENASE
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Provided are certain IDO inhibitors, pharmaceutical compositions thereof, and methods of use thereof.
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Paragraph 210-211
(2018/06/12)
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- PYRROLO[2,3-C]PYRIDINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF IN MEDICINE
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Disclosed are a pyrrolo[2,3-c]pyridine derivative, a preparation method therefor, and use thereof in medicine. Specifically, disclosed are a pyrrolo[2,3-c]pyridine derivative as represented by general formula (1), a preparation method therefor, a pharmaceutical composition comprising the derivative, as well as use thereof as a BRD4 inhibitor in the treatment of related diseases such as cancers, inflammations, chronic liver diseases, diabetes, cardiovascular diseases and AIDS, each substituent in general formula (I) being same as defined in the description.
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Page/Page column 50
(2018/08/03)
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- Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines
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A copper-catalyzed oxidative decarboxylative coupling of α-keto acids with NH-sulfoximines has been developed. With CuBr as the catalyst and K2S2O8 as the oxidant, this reaction enables the formation of a C-N bond and gives N-aroylsulfoximine products in moderate to excellent yields. The reaction mechanism is likely to involve the generation of a reactive aroyl radical intermediate.
- Pimpasri, Chaleena,Sumunnee, Ladawan,Yotphan, Sirilata
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supporting information
p. 4320 - 4327
(2017/07/10)
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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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- Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate
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A metal-free and operationally simple N-arylation of NH-sulfoximines with aryne precursors is reported. Transition metal-free reaction conditions and shorter reaction times are the highlights of the present method. The mild optimized condition was also found to be suitable with enantiopure substrates.
- Aithagani, Sravan Kumar,Dara, Saidulu,Munagala, Gurunadham,Aruri, Hariprasad,Yadav, Mahipal,Sharma, Shweta,Vishwakarma, Ram A.,Singh, Parvinder Pal
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supporting information
p. 5547 - 5549
(2015/12/01)
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- Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
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As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
- Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
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p. 5594 - 5602
(2015/09/01)
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- General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor
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The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clinical candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesising a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, commercially available precursor is discussed.
- Goldberg, Frederick W.,Kettle, Jason G.,Xiong, Jian,Lin, Daoguang
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p. 6613 - 6622
(2015/03/30)
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- N-arylations of sulfoximines with 2-arylpyridines by copper-mediated dual N-H/C-H activation
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A high-yielding method providing rapid access to new N-arylated sulfoximines has been developed. A stoichiometric amount of copper facilitates the C-H activation of 2-arylpyridines which then undergo oxidative C-N cross-couplings with various sulfoximine derivatives.
- Wang, Long,Priebbenow, Daniel L.,Dong, Wanrong,Bolm, Carsten
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supporting information
p. 2661 - 2663
(2014/06/09)
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- Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes
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Sulfoximines direct: A new protocol for the chemo-and regioselective ortho C-H acetoxylation of arenes in N-benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the C-H oxidation product through acid-promoted hydrolysis, isolated, and reused (see scheme). The meta-substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine is preserved in this transformation. C(sp3)-H acetoxylation of the methyl group is also demonstrated.
- Yadav, M. Ramu,Rit, Raja K.,Sahoo, Akhila K.
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supporting information; experimental part
p. 5541 - 5545
(2012/06/01)
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- NOVEL SULPHOXIMINE-SUBSTITUTED QUINAZOLINE AND QUINAZOLINE DERIVATIVES AS KINASE INHIBITORS
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The present invention relates to a quinoline or quinazoline derivative having the general formula (A): in which R3, R4, W, Y and Q are indicated in the description and the claims, the use of the compounds of the general formula (A) f
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Page/Page column 31
(2009/01/20)
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- Generation of oxynitrenes and confirmation of their triplet ground states
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New sulfoximine- and phenanthrene-based photochemical precursors to oxynitrenes have been developed. These precursors have been used to examine the chemistry and spectroscopy of oxynitrenes. The first EPR spectra of oxynitrenes are reported and are consistent with their triplet ground states. Additional support for the triplet ground state of oxynitrenes is provided by trapping and reactivity studies, nanosecond time-resolved IR investigations, and computational studies.
- Wasylenko, Walter A.,Kebede, Naod,Showalter, Brett M.,Matsunaga, Nikita,Miceli, Alexander P.,Liu, Yonglin,Ryzhkov, Lev R.,Hadad, Christopher M.,Toscano, John P.
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p. 13142 - 13150
(2008/03/11)
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- Electrochemical Imination of Sulfoxides Using N-Aminophthalimide
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(Equation Presented) A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.
- Siu, Tung,Yudin, Andrei K.
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p. 1839 - 1842
(2007/10/03)
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- COPPER CATALYZED REACTIONS OF S,S-DIARYL-N-TOSYLSULFILIMINES WITH SULFOXIDES: NEW SYNTHESIS OF N-TOSYLSULFOXIMINES
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S,S-Diaryl-N-tosylsulfilimines were readily reduced by treatment with copper to give the corresponding sulfides and a copper-tosylnitrenoid-complex which upon reacting with sulfoxides afforded the corresponding N-tosylsulfoximines, derived from sulfoxides in fair yields.When optically active (-)-(S)-methylphenyl sulfoxide was used, the corresponding (+)-N-tosylsulfoximine was obtained together with the sulfide derived from the N-tosylsulfilimine.The stereochemical course of the conversion of (-)-(S)-sulfoxide to (+)-N-tosylsulfoximine was found to be mainly retention (76percent) with partial racemization due to thermal pyramidal inversion of the starting sulfoxide.
- Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
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p. 213 - 222
(2007/10/02)
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- A FACILE CONVERSION OF SULFOXIMINES AND SULFONEDIIMINES TO SULFOXIDES AND SULFILIMINES WITH TERT-BUTYL NITRITE
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N-Unsubstituted sulfoximines and N-mono-tosylsulfonediimines were found to react readily with tert-butyl nitrite to give the corresponding sulfoxides and N-tosylsulfilimines in high yields with no racemization.
- Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
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p. 369 - 374
(2007/10/02)
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- REDUCTIVE DEIMINATION OF SULFOXIMIDES AND SULFIMIDES WITH P-TOLUENESULFONYL NITRITE AND T-BUTYL THIONITRATE
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Reduction of sulfimides and sulfoximides with p-toluenesulfonyl nitrite, a new nitrosating agent, gave nearly quantitatively the corresponding deimination products, sulfides and sulfoxides, respectively.In the reaction of dialkyl and aryl alkyl sulfoximides with t-butyl thionitrate, N-t-butylthiosulfoximides were obtained besides the usual deimination products, although diaryl sulfoximides were readily deiminated to the corresponding sulfoxides in good yields in the same treatment. t-Butyl thionitrsate was also found to deiminate diphenyl sulfimide to give diphenyl sulfide in good yield.Sulfoximides reacted sluggishly with t-butyl thionitrite, however, eventually affording a small amount of sulfoxides.
- Oae, Shigeru,Iida, Kazuyuki,Takata, Toshikazu
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p. 103 - 114
(2007/10/02)
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