- A Highly Enantioselective Asymmetric Hydrogenation Route to β-(2R,3S)-Methyltryptophan
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Asymmetric hydrogenation of a protected (Z)-dehydro-β-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97percent ee.Deprotection then afforded (2R,3S)-β-methyltryptophan 1.
- Hoerrner, R. Scott,Askin, David,Volante, R. P.,Reider, Paul J.
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- NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN
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The present invention concerns novel pyridin-2(1H)one derivatives, their process of preparation and their use in therapeutics, in particular as agents for treating and/or preventing pain.
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Page/Page column 15; 22-23
(2021/04/10)
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- Pyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia
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Mechanical Allodynia (MA), a frequent chronic pain symptom caused by innocuous stimuli, constitutes an unmet medical need, as treatments using analgesics available today are not always effective and can be associated with important side-effects. A series of 3,5-disubstituted pyridin-2(1H)-ones was designed, synthesized and evaluated in vivo toward a rat model of inflammatory MA. We found that the series rapidly and strongly prevented the development of MA. 3-(2-Bromophenyl)-5-(phenylamino)pyridin-2(1H)-one 69, the most active compound of the series, was also able to quickly reverse neuropathic MA in rats. Next, when 69 was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biological target(s), we found that 69 is a p38α MAPK inhibitor, a PK known to contribute to pain hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones thus could represent a novel class of analgesic for the treatment of MA.
- Abrunhosa-Thomas, Isabelle,Anizon, Fabrice,Artola, Alain,Dallel, Radhouane,Descheemaeker, Amélie,Giraud, Francis,Moreau, Pascale,Nauton, Lionel,Pinto-Pardo, Nicolas,Théry, Vincent,Visseq, Alexia
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- Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids
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Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in
- Das, Amrita,Watanabe, Kenji,Morimoto, Hiroyuki,Ohshima, Takashi
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supporting information
p. 5794 - 5797
(2017/11/10)
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- Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
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Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
- Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
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p. 734 - 745
(2016/01/15)
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- 4-Substituted Pyrrolo[2,3-d]pyrimidine Compound and Use Thereof
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The invention relates to a 4-substituted pyrrolo[2,3-d]pyrimidine compound and the use thereof in preparing medications for treating JAK-targeted diseases such as rheumatoid, immune system diseases, and tumor. The 4-substituted pyrrolo[2,3-d]pyrimidine compound of the invention is as shown in chemical formula I. The activity experimental results of the invention show that the new compound has obvious effect and activity in inhibition of Janus kinases, JAK-STAT, cell proliferation of human lymphocytoma, and rheumatoid arthritis.
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Paragraph 0045; 0046; 0071; 0072; 0095; 0096
(2016/12/07)
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- Au-Catalyzed Cross-Coupling of Arenes via Double C-H Activation
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The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds. The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.
- Cambeiro, Xacobe C.,Ahlsten, Nanna,Larrosa, Igor
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supporting information
p. 15636 - 15639
(2016/01/09)
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- NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE
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Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the said compound, and the organic electronic device uses the said organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.
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Paragraph 0126; 0127
(2013/07/31)
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- NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE
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Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. This nitrogen-containing aromatic compound is represented by the general formula (1). Further, the present invention relates to or
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Paragraph 0143
(2013/09/11)
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- Asymmetric synthesis of indole homo-Michael adducts via dynamic kinetic Friedel-Crafts alkylation with cyclopropanes
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An enantioconvergent Friedel-Crafts alkylation of indoles with donor-acceptor cyclopropanes is described. The reaction is catalyzed by pybox?MgI2 and proceeds via a type I dynamic kinetic asymmetric transformation (DyKAT).
- Wales, Steven M.,Walker, Morgan M.,Johnson, Jeffrey S.
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supporting information
p. 2558 - 2561
(2013/07/11)
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- Cooperative catalytic activation of Si-H bonds by a polar Ru-S bond: Regioselective low-temperature c-h silylation of indoles under neutral conditions by a Friedel-crafts mechanism
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Merging cooperative Si-H bond activation and electrophilic aromatic substitution paves the way for C-3-selective indole C-H functionalization under electronic and not conventional steric control. The Si-H bond is heterolytically split by the Ru-S bond of a coordinatively unsaturated cationic ruthenium(II) complex, forming a sulfur-stabilized silicon electrophile. The Wheland intermediate of the subsequent Friedel-Crafts-type process is assumed to be deprotonated by the sulfur atom, no added base required. The overall catalysis proceeds without solvent at low temperature, only liberating dihydrogen.
- Klare, Hendrik F. T.,Oestreich, Martin,Ito, Jun-Ichi,Nishiyama, Hisao,Ohki, Yasuhiro,Tatsumi, Kazuyuki
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supporting information; experimental part
p. 3312 - 3315
(2011/04/24)
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- Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: Asymmetric synthesis of allyl oxindoles
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The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee. Copyright
- Linton, Elizabeth C.,Kozlowski, Marisa C.
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supporting information; experimental part
p. 16162 - 16163
(2009/05/09)
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- Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'
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An atom-economic Pd0-catalyzed synthesis of a series of pinacol-type indolylboronates 3 from the corresponding bromoindole substrates 2 and pinacolborane (pinBH) as borylating agent was elaborated. The optimal catalyst system consisted of a 1:2 mixture of [Pd(OAc)2] and the ortho-substituted biphenylphosphine ligand L-3 (Scheme 4, Table). Our synthetic protocol was applied to the fast, preparative-scale synthesis of 1-substituted indolylboronates 3a-h in the presence of different functional groups, and at a catalyst load of only 1 mol-% of Pd.
- Stadlwieser, Josef F.,Dambaur, Markus E.
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p. 936 - 946
(2007/10/03)
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- Oxidative C-arylation of free (NH)-heterocycles via direct (sp3) C-H bond functionalization
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The development of a new chemical transformation, namely oxidative C-arylation of saturated (NH)-heterocycles, is described. This reaction combines dehydrogenation and arylation in one process, leading to cross-coupling of (NH)-heterocycles and haloarenes. Typical reaction conditions involve heating the reaction partners in anhydrous dioxane at 120-150 °C in the presence of RhCl(CO)[P(Fur)3]2 as the catalyst and Cs2CO3 as the base. Addition of tert-butylethylene as the hydrogen acceptor increases the chemical yield by diminishing the dehalogenation pathway. This method demonstrated a good substrate scope, allowing for cross-coupling of a variety of (NH)-heterocycles (e.g., pyrrolidine, piperidine, piperazine, morpholine) and halo(hetero)arenes to afford valuable heterocyclic products in one step. The preliminary mechanistic studies provided some insight regarding the key events in the proposed catalytic cycle, including β-hydride elimination of an amido rhodium complex and carbometalation of the resulting imine. A large kinetic isotope effect [KIE (kC-H/kC-D) = 4.3] suggests that one or both β-hydride elimination steps are rate determining. The central role for the phosphine ligand was established in controlling the partitioning between the oxidative C-arylation and N-arylation pathways. Copyright
- Sezen, Bengue,Sames, Dalibor
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p. 13244 - 13246
(2007/10/03)
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- Reactions of a nitrodienamine with 1-protected indolyllithium
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Reactions of a nitrodienamine (1) with indolyllithiums prepared from 1-protected indole derivatives were investigated.
- Koike, Takeshi,Shinohara, Yoshifumi,Tobinaga, Seisho,Takeuchi, Naoki
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p. 2701 - 2708
(2007/10/03)
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- 3-lithio-1-(triisopropylsilyl)indole, preparation and reactions with electrophilic reagents
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3-Lithio-1-(triisopropylsilyl)indole (2) is prepared by halogenmetal exchange from the corresponding 3-bromoindole and regioselectively reacts with a variety of electrophilic reagents to give 3-substituted indoles.
- Amat, Mercedes,Sathyanarayana, Swargam,Hadida, Sabine,Bosch, Joan
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p. 1713 - 1718
(2007/10/03)
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- Synthesis and absolute configuration of (+)-hapalindole Q
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The versatility of brominated camphor derivatives as six-membered-ring chiral building blocks in the synthesis of compounds of mixed biogenesis has been demonstrated in an eight-step synthesis of (+)-hapalindole Q from (+)-(1R)-9-bromocamphor in an overall 8% yield which confirms the absolute stereochemistry to be 10R, 11R, 12R, 15R.
- Vaillancourt, Valerie,Albizati, Kim F.
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p. 3499 - 3502
(2007/10/02)
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