- Selective and one-pot formation of phenols by anodic oxidation
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Direct monohydroxylation of benzene and substituted benzenes was successfully performed by anodic oxidation to form the corresponding phenol derivatives in good yields. The anodic oxidation was generally carried out in a mixed solvent of trifluoroacetic acid and dichloromethane containing triethylamine using a divided cell equipped with a platinum plate as the anode, a carbon rod as the cathode. Benzene derivatives having electron withdrawing groups were suitable for the present electrochemical oxidation. It was clarified that aryltrifluoroacetates were formed as the initial products from the reaction of the radical cations, generated by one electron transfer from the substrates, with trifluoroacetic acid, followed by hydrolysis during work-up to give the corresponding phenols.
- Fujimoto, Kazuo,Tokuda, Yuichiro,Maekawa, Hirofumi,Matsubara, Yoshiharu,Mizuno, Takumi,Nishiguchi, Ikuzo
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Read Online
- Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
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A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
- Huang, You,Li, Xiaohu
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supporting information
p. 9934 - 9937
(2021/10/12)
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- Preparation method of benzofuran derivative
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The invention discloses a preparation method for synthesizing a benzofuran derivative. The specific implementation method is as shown in the specification. The method has novel synthetic route, simpleand convenient operation, high yield, and good safety, and is suitable for industrial production. A novel synthetic method of an intermediate VI is also designed, a Wittig reaction is carried out, and then ring-closing is carried out to obtain a benzofuran ring.
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- Fullerene-Filled Liquid-Crystal Stars: A Supramolecular Click Mechanism for the Generation of Tailored Donor–Acceptor Assemblies
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Two shape-persistent star mesogens with oligo(phenylene ethenylene) arms and a phthalocyanine core—one providing free space (2) and one sterically encumbered by four fullerenes attached through spacers (3)—have been successfully synthesized. In contrast to the smaller discotic derivative 1, mesogen 2 forms a columnar liquid crystal (LC), which can only be partially aligned without π-stacking, while 3 is not an LC. Exceptionally, the 1:1 mixture of 2 and 3 forms an alignable columnar LC with strong π-stacking and quadruply helically organized fullerenes by an unprecedented click process that is similar to a ball detent mechanism. The C60 units also interconnect different columns. This is driven by nanosegregation and space-filling of the voids with fullerenes. Photophysical studies confirm the presence of a light-collecting system that generates charge-separated states in solution and in the solid state, which makes such highly organized materials attractive for the study of future photovoltaic devices.
- Lehmann, Matthias,Dechant, Moritz,Holzapfel, Marco,Schmiedel, Alexander,Lambert, Christoph
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supporting information
p. 3610 - 3615
(2019/02/09)
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- Synthesis method of methyl 4-formyl-3-hydroxybenzoate
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The invention discloses a synthesis method of methyl 4-formyl-3-hydroxybenzoate. The method includes the following step that methyl 3-hydroxybenzoate as a raw materials reacts with paraformaldehyde under the action of Lewis acid and an organic base to obt
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Paragraph 0039-0054
(2019/11/20)
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- PROCESSES FOR PREPARATION OF (S)-TERT-BUTYL 4,5-DIAMINO-5-OXOPENTANOATE
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Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.
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Paragraph 00383-00387
(2019/03/12)
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- HDAC6 INHIBITORS AND IMAGING AGENTS
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Provided herein are compounds useful for binding to one or more histone deacetylase enzymes (HDACs). The present application further provides radiolabeled compounds useful as a radiotracer for position emission tomography imaging of HDAC. Methods for prep
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- Design, synthesis, and structure-activity relationship of a novel series of GluN2C-selective potentiators
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NMDA receptors are tetrameric complexes composed of GluN1 and GluN2A-D subunits that mediate a slow Ca2+-permeable component of excitatory synaptic transmission. NMDA receptors have been implicated in a wide range of neurological diseases and thus represent an important therapeutic target. We herein describe a novel series of pyrrolidinones that selectively potentiate only NMDA receptors that contain the GluN2C subunit. The most active analogues tested were over 100-fold selective for recombinant GluN2C-containing receptors over GluN2A/B/D-containing NMDA receptors as well as AMPA and kainate receptors. This series represents the first class of allosteric potentiators that are selective for diheteromeric GluN2C-containing NMDA receptors.
- Zimmerman, Sommer S.,Khatri, Alpa,Garnier-Amblard, Ethel C.,Mullasseril, Praseeda,Kurtkaya, Natalie L.,Gyoneva, Stefka,Hansen, Kasper B.,Traynelis, Stephen F.,Liotta, Dennis C.
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supporting information
p. 2334 - 2356
(2014/04/17)
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- NMDA RECEPTOR MODULATORS AND USES RELATED THERETO
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This disclosure relates to NMDA modulators and used related thereto such as for treatment of central nervous system disorders. In certain embodiments, compounds disclosed herein are NR2C subunit-selective NMDA potentiators. In certain embodiments, the disclosure contemplates compounds and pharmaceutical compositions. In certain embodiments, the disclosure contemplates compounds disclosed herein as prodrugs, optionally substituted with one or more substituents, derivatives, or salts thereof. In certain embodiments, the disclosure relates to methods of treating or preventing nervous system disorders comprising administering an effective amount of a composition comprising compound disclosed herein to a subject in need thereof.
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Page/Page column 26; 27; 32;35
(2014/03/21)
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- 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
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Compounds of formula (I) described herein are inhibitors of the phosphodiesterase 4 (PDE4) enzyme and are useful for the prevention and/or treatment of an allergic disease state or a disease of the respiratory tract characterized by airway obstruction.
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Paragraph 0617; 0618
(2014/06/23)
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- Synthetic remodeling of the chartreusin pathway to tune antiproliferative and antibacterial activities
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Natural products of the benzonaphthopyranone class, such as chartreusin, elsamicin A, gilvocarcin, and polycarcin, represent potent leads for urgently needed anticancer therapeutics and antibiotics. Since synthetic protocols for altering their architectur
- Ueberschaar, Nico,Xu, Zhongli,Scherlach, Kirstin,Metsae-Ketelae, Mikko,Bretschneider, Tom,Dahse, Hans-Martin,Goerls, Helmar,Hertweck, Christian
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supporting information
p. 17408 - 17416
(2014/01/06)
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- BENZOXAZEPIN COMPOUNDS SELECTIVE FOR PI3K P110 DELTA AND METHODS OF USE
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Benzoxazepin Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.
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Page/Page column 105
(2012/10/08)
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- CARBAMOYL-TYPE BENZOFURAN DERIVATIVES
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The present invention provides a carbamoyl-type benzofuran derivative of the formula [1]: wherein Ring Z is a group of the formula: etc.; A is a single bond, and the like; Y is a cycloalkanediyl group, etc.; R4 and R5 are the same or different and each is an optionally substituted lower alkyl group, etc.; R1 is a halogen atom, etc.; Ring B of the formula: is an optionally substituted benzene ring; and R3 is a hydrogen atom, etc., or a pharmaceutically acceptable salt thereof, which is useful as an FXa inhibitor.
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Page/Page column 90
(2008/06/13)
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- Synthesis and physical properties of novel liquid crystals containing pyranobenzopyrans as a core structure
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The synthesis and physical properties of pyranobenzopyran ring system have been studied as a core structure of novel liquid crystal (LC) compounds. Substituted pyranobenzopyrans having an alkoxy group on the A ring (benzene ring) exhibited smectic and nematic phase, those having a fluoro-substituted phenyl group on the A ring exhibited wider range of smectic phase. When the latter are added to a base LC mixture (ZLI-1565, Merck), the clearing point was raised. Interestingly, pyranobenzopyrans having a trifluoromethyl phenyl group or a cyano group on the A ring showed an extremely large positive dielectric anisotropy. The Royal Society of Chemistry 2005.
- Inoue, Seiichi,Yanai, Takayoshi,Ando, Shinji,Nakazawa, Akinori,Honda, Kiyoshi,Hoshino, Yujiro,Asai, Tomoyuki
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p. 4746 - 4752
(2007/10/03)
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- BENZOFURAN DERIVATIVE
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The present invention provides a benzofuran derivative of the formula [1]: wherein x is a group of the formula: -N="or" -CH=; Y is an optionally substituted amino group, an optionally substituted cycloalkyl group or an optionally substituted saturated heterocyclic group; A is a single bond, a carbon chain optionally having a double bond within or at the end(s) of the chain, or an oxygen atom; R1 is a hydrogen atom or a halogen atom; Ring B is an optionally substituted benzene ring; and R3 is a hydrogen atom, or a pharmaceutically acceptable salt thereof, which is useful as a medicament, especially as an activated blood coagulation factor X inhibitor.
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- The synthesis and evaluation of benzofuranones as β-lactamase substrates
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6- and 7-Carboxy-3-phenylacetamido-3H-1-benzofuran-2-one have been synthesized as potential β-lactamase substrates and/or inhibitors. These compounds were prepared by lactonization of the corresponding, appropriately substituted phenylglycines. The latter compounds were prepared by either the Strecker or the Buecherer-Berg method. The benzofuran-2-ones were less stable in aqueous solution than the analogous acyclic phenaceturate esters but comparably stable to analogous benzopyran-2-ones. They differed from the latter compounds however in that the C-3 hydrogen of the furan-2-ones, adjacent to the lactone carbonyl group, was distinctly acidic; 7-carboxy-3-phenylacetamido-3H-1-benzofuran-2-one exists largely as an enolate at pH 7.5. The furan-2-ones were β-lactamase substrates with reactivity very similar to the analogous acyclic phenaceturates. They were not, however, DD-peptidase inhibitors and are thus unlikely to have antibiotic activity. The structural basis for these observations is discussed.
- Adediran,Cabaret,Drouillat,Pratt,Wakselman
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p. 1175 - 1183
(2007/10/03)
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- Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II: Synthesis of bromo- and methoxycarbonylcoumarins
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Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (1e). The substituent effects are discussed. A substituent at C6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.
- Harayama,Nakatsuka,Nishioka,Murakami,Hayashida,Ishii
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p. 2170 - 2173
(2007/10/02)
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