- Five-membered heteroaromatic derivative, preparation method and application thereof
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The invention belongs to the technical field of medicines, and particularly relates to a five-membered heteroaromatic compound, a composition, a preparation method and application thereof. The compound or the composition can be used as an inhibitor of a retinoid-related orphan receptor [gamma]t (ROR [gamma]t). The invention also relates to a method for preparing the compound and the composition, and application of the compound and the composition in treatment or prevention of ROR [gamma]t-mediated cancers, inflammations or autoimmune diseases of mammals, especially human beings.
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Paragraph 0968-0971
(2021/07/08)
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- One-Pot and Reducible-Functional-Group-Tolerant Synthesis of α-Aryl- and α-Heteroaryl-α-Trifluoromethyl Alcohols via Tandem Trifluoroacetylation and MPV Type Reduction
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We have developed a new one-pot synthesis of α-aryl- and α-heteroaryl-α-trifluoromethyl alcohols carrying not only arenes with electron-withdrawing groups but also electron-deficient nitrogen-containing heteroarenes, which are of increasing interest becau
- Funabiki, Kazumasa,Hayakawa, Ayaka,Kani, Ryunosuke,Inuzuka, Toshiyasu,Kubota, Yashuhiro
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p. 5978 - 5984
(2019/08/30)
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- Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands
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The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.
- Brüning, Fabian,Nagae, Haruki,K?ch, Daniel,Mashima, Kazushi,Togni, Antonio
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supporting information
p. 10818 - 10822
(2019/07/31)
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- Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines
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A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of N-sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.
- Hirano, Kazuki,Gondo, Satoshi,Punna, Nagender,Tokunaga, Etsuko,Shibata, Norio
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p. 406 - 410
(2019/02/13)
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- Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates
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A palladium-catalyzed C(sp3)?C(sp2) Suzuki–Miyaura cross-coupling of aryl boronic acids and α-(trifluoromethyl)benzyl tosylates is reported. A readily available, air-stable palladium catalyst was employed to access a wide range of functionalized 1,1-diaryl-2,2,2-trifluoroethanes. Enantioenriched α-(trifluoromethyl)benzyl tosylates were found to undergo cross-coupling to give the corresponding enantioenriched cross-coupled products with an overall inversion in configuration. The crucial role of the CF3 group in promoting this transformation is demonstrated by comparison with non-fluorinated derivatives.
- Brambilla, Marta,Tredwell, Matthew
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supporting information
p. 11981 - 11985
(2017/09/20)
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- Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources
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The trifluoromethylation of carbonyl compounds is accomplished by the stable (trifluoromethyl)zinc reagent generated and then isolated from CF3I and ZnEt2, which can be utilized as a trifluoromethyl anion source (CF3-). The reaction proceeds smoothly with diamine as a ligand and ammonium salt as an initiator, providing the corresponding trifluoromethylated alcohol products. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source (:CF2) not only for gem-difluoroolefination of carbonyl compounds with phosphine but also for gem-difluorocyclization of alkenes or alkynes via the thermal decomposition, respectively.
- Aikawa, Kohsuke,Toya, Wataru,Nakamura, Yuzo,Mikami, Koichi
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supporting information
p. 4996 - 4999
(2015/11/03)
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- Photoinduced additive-free trifluoromethylation of aromatic aldehydes with TMSCF3
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We report herein a new and effective method for additive-free trifluoromethylation of aromatic aldehydes with TMSCF3. Normal acidic hydrolysis for desilylation in the workup process is not required in this transformation. This reaction presents
- Sun, Jing,Peng, Xinhua,Guo, Hao
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supporting information
p. 797 - 800
(2015/01/30)
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- Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines
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In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction
- Martinelli, Emilie,Vicini, Anna Chiara,Mancinelli, Michele,Mazzanti, Andrea,Zani, Paolo,Bernardi, Luca,Fochi, Mariafrancesca
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supporting information
p. 658 - 660
(2015/01/09)
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- FUNGICIDAL COMPOSITIONS
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The present invention provides a composition comprising a combination of components A) and B), wherein component A) is a compound of formula (I) and the component (B) is a further fungicide, insecticide or herbicide.
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Paragraph 1360-1362
(2014/11/27)
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- Efficient synthesis of [18F]trifluoromethane and its application in the synthesis of PET tracers
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A new strategy towards [18F]trifluoromethyl-containing compounds is developed. [18F]trifluoromethane is synthesised in a fast and efficient manner and subsequently used in the reaction with aldehydes and ketones forming [18/sup
- Van Der Born, Dion,Herscheid,Orru, Romano V.A.,Vugts, Danielle J.
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supporting information
p. 4018 - 4020
(2013/07/26)
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- FUNGICIDAL COMPOSITIONS
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The present invention provides a composition comprising a combination of components A) and B), wherein component A) is a compound of formula (I) and the component (B) is a further fungicide, insecticide or herbicide.
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Page/Page column 377
(2012/11/13)
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- KYNURENINE PRODUCTION INHIBITOR
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Provided is a kynurenine production inhibitor comprising a nitrogen-containing heterocyclic compound represented by formula (I): (wherein R50 and R51 may be the same or different and each represent a hydrogen atom or the like, G1 and G2 may be the same or different and each represent a nitrogen atom or the like, X represents formula (III): (wherein m1 and m2 may be the same or different and each represent an integer of 0 or 1, Y represents an oxygen atom or the like, and R6 and R7 may be the same or different and each represent a hydrogen atom or the like), R1 represents optionally substituted lower alkyl or the like, R2 represents a hydrogen atom or the like, and R3 represents optionally substituted lower alkyl or the like), and the like.
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Page/Page column 132
(2011/10/12)
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- Chemoselective reduction of ketones: Trifluoromethylketones versus methylketones
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Treatment of an equimolar mixture of trifluoromethylketones (TFMKs) and methylketones (MKs) with Et2Zn resulted in selective reduction of the TFMKs in good yield. In contrast, treatment of an equimolar mixture of TFMKs and MKs with NaBH4 in the presence of CeCl3 in EtOH/H 2O (10:1) at -10°C reduced only the MKs.
- Sasaki, Shigeru,Yamauchi, Takayasu,Kubo, Hajime,Kanai, Masatomi,Ishii, Akihiro,Higashiyama, Kimio
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p. 1497 - 1500
(2007/10/03)
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- Remarkably Facile Solvolyses of Triflates via Carbocationic Processes in Dimethyl Sulfoxide
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A number of triflates have been shown to undergo clean pseudo-first-order solvolysis reactions in DMSO-d6 to give products derived from carbocationic intermediates. Thus, t-BuCH(OTf)CO-t-Bu (5) and t-BuCH 2OTf (9) react readily in DMSO-d6 at 25 °C to give a rearranged oxosulfonium salts, and subsequent alkene products where methyl migration to the incipient cationic center occurs. t-BuCH(OTf)CO 2CH3 (14) gives analogous rearranged products, and 1-methylcyclopropyl triflate (21) gives a ring-opened allylic oxosulfonium salt. These triflates react primarily via kΔ pathways. 6-Methylbicyclo[3.1.0]hex-6-yl triflate (23), bicyclo[2.2.1hept-1-yl triflate (24), 1,6-methano[10]-annulen-11-yl triflate (25), (CH3) 2C(OTf)CO2CH3 (26), and (CH3) 2CCN(OTf) (29) all react in DMSO-d6 to give carbocation-derived products. PhCH(OTf)CF3 (33) and substituted analogues also react readily in DMSO-d6, and the Hammett ρ + value is -3.7. This suggests a "borderline" mechanism where the transition state has substantial charge development. The primary feature of these solvolyses is the high reactivity of all of these triflates in DMSO-d6. Thus, these triflates are all more reactive in DMSO-d 6 than in HOAc, and for most, rates are faster than in CF 3CH2OH. Triflates 5, 21, 29, and 33 are 10 8-109 times more reactive in DMSO-d6 than the corresponding mesylates. It is suggested that the decreased need for electrophilic solvation of trifiate anion, and the high cation solvating ability of DMSO, are the reasons for the high triflate reactivity in DMSO-d 6.
- Creary, Xavier,Burtch, Elizabeth A.
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p. 1227 - 1234
(2007/10/03)
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- Microreactors for the synthesis of fluorinated materials
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The utility of microreactor for the synthesis of α-fluoro-α, β-unsaturated esters, trifluoromethylation and Michael addition reaction, is described.
- Miyake, Noriaki,Kitazume, Tomoya
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p. 243 - 246
(2007/10/03)
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- A chiral triaminosulfonium salt: Design and application to catalytic asymmetric synthesis
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The first chiral triaminosulfonium salt, tris((S,S)-3,4-diphenylpyrrolidino)sulfonium difluorotriphenylstannate, catalyzes trifluoromethylation of benzaldehyde with (trifluoromethyl)trimethylsilane to give the corresponding optically active alcohol with 52% ee.
- Kuroki, Yoshichika,Iseki, Katsuhiko
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p. 8231 - 8234
(2007/10/03)
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