- The improved preparation of 7,8-dihydro-quinoline-5(6H)-one and 6,7- dihydro-5H-1-pyrindin-5-one
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Compounds 7,8-dihydroquinoline-5(6H)-one (3) and 6,7-dihydro-5H-1- pyrindin-5-one (5) are formed by new methods from 1,3-diketone compound, ammonium acetate and 1,1,3,3-tetraethoxylpropane.
- Huang, Yanhe,Hartmann, Rolf W.
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- Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
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An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.
- Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin
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supporting information
p. 7445 - 7449
(2021/10/02)
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- Preparation method of 6,7-dihydro-5H-cyclopentadieno[b] pyridine-5-one
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The invention provides a preparation method of 6,7-dihydro-5H-cyclopentadieno[b] pyridine-5-one, and the preparation method comprises the following steps: by using a compound (I) as a substrate, Fe as a catalyst, a 50% hydrogen peroxide aqueous solution as an oxide and acetonitrile as a solvent, reacting at 50 DEG C for 24 hours to obtain a crude product, and carrying out column chromatography to obtain a pure compound (II). The method for preparing the compound (II) is mild in reaction condition, easy to purify, simple to operate and high in yield.
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Paragraph 0011-0014
(2019/12/29)
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- Electrochemical benzylic oxidation of C-H bonds
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Oxidized products have become increasingly valuable as building blocks for a wide variety of different processes and fine chemistry, especially in the benzylic position. We report herein a sustainable protocol for this transformation through C-H functionalization and is performed using electrochemistry as the main power source and tert-butyl hydroperoxide as the radical source for the C-H abstraction. The temperature conditions reported here do not increase above 50 °C and use an aqueous-based medium. A broad substrate scope is explored, along with bioactive molecules, to give comparable and increased product yields when compared to prior reported literature without the use of electrochemistry.
- Marko, Jason A.,Durgham, Anthony,Bretz, Stacey Lowery,Liu, Wei
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supporting information
p. 937 - 940
(2019/01/23)
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- Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions
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An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.
- Yu, Han,Zhao, Qixin,Wei, Zheyu,Wu, Zhikang,Li, Qi,Han, Sheng,Wei, Yongge
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supporting information
p. 7840 - 7843
(2019/07/12)
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- GHRELIN O-ACYLTRANSFERASE INHIBITORS
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This invention relates to novel compounds according to Formula (I) which are inhibitors of ghrelin O-acyltransferase (GOAT), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy for the treatment
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Page/Page column 63; 83; 84
(2019/08/26)
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- Selective C(sp3)?H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
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A mild and selective C(sp3)?H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C?H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (?)-ambroxide, pregnenolone acetate, (+)-sclareolide, and artemisinin, exemplifies the utility of this new method.
- Laudadio, Gabriele,Govaerts, Sebastian,Wang, Ying,Ravelli, Davide,Koolman, Hannes F.,Fagnoni, Maurizio,Djuric, Stevan W.,No?l, Timothy
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supporting information
p. 4078 - 4082
(2018/03/21)
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- Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds
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A continuous mesofluidic process has been developed for benzylic C-H oxidation with moderate to good yields using a photocatalyst (riboflavin tetraacetate, RFT) activated by a UV lamp and an iron additive [Fe(ClO4)2] via incorporation of singlet oxygen (1O2) for the direct formation of oxidized C=O or CH-OH compounds.
- Lesieur, Mathieu,Genicot, Christophe,Pasau, Patrick
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supporting information
p. 1987 - 1990
(2018/04/16)
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- Ketone or aldehyde synthetic method by using manganese compound to conduct catalytic oxidation of pyridine compound
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The present invention discloses a ketone or aldehyde synthetic method by using a manganese compound to conduct catalytic oxidation of a pyridine compound. Pyridine compounds containing substituent groups are used as a reaction substrate, the manganese compound is used as a catalyst, one or more than two of water, tertiary butanol, acetonitrile, ethyl acetate, or dichloromethane are used as a solvent, a peroxide is used as an oxygen source, a reaction is conducted at a temperature of 25-50 DEG C for 12-48 h, so that the C-H bond of the side chain of the pyridine is oxidized to an ketone or aldehyde by one step, and a reaction crude product is processed to obtain a final product. The preparation method is mild in reaction conditions, less in catalyst use amount, high in atom economy, and simple in operation, has a wide suitable range of substrates, and has industrial applicability.
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Paragraph 0027; 0028
(2016/12/01)
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- Direct oxidation of the Csp3–H bonds of N-heterocyclic compounds to give the corresponding ketones using a reusable heterogeneous MnOx-N@C catalyst
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Novel reusable MnOx-N@C catalyst has been developed for the direct oxidation of N-heterocycles under solvent-free conditions using TBHP as benign oxidant to give the corresponding N-heterocyclic ketones. The catalytic system exhibited a broad substrate scope and excellent regioselectivity, as well as being amenable to gram-scale synthesis. This MnOx-N@C catalyst also showed good reusability and was successfully recycled six times without any significant loss of activity.
- Ren, Lanhui,Wang, Lianyue,Lü, Ying,Li, Guosong,Gao, Shuang
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p. 1216 - 1221
(2016/09/07)
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- SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE
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Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.
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Page/Page column 571
(2016/04/10)
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- NOVEL PYRROLIDINE DERIVED BETA 3 ADRENERGIC RECEPTOR AGONISTS
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The present invention provides compounds of Formula (I), pharmaceutical compositions thereof, and method of using the same in the treatment or prevention of diseases mediated by the activation of β3-adrenoceptor.
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Page/Page column 69
(2015/04/22)
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- SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
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Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.
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Page/Page column 33
(2008/12/04)
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- Development of orally active oxytocin antagonists: Studies on 1-(1-{4- [1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy].2methoxybenzoyl}- 4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines
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The previously reported oxytocin antagonist L-371,257 (2) has been modified at its acetylpiperidine terminus to incorporate various pyridine N- oxide groups. This modification has led to the identification of compounds with improved pharmacokinetics and excellent oral bioavailability. The pyridine N-oxide series is exemplified by L-372,662 (30), which possessed good potency in vitro (Ki = 4.1 nM, cloned human oxytocin receptor) and in vivo (intravenous AD50 = 0.71 mg/kg in the rat), excellent oral bioavailability (90% in the rat, 96% in the dog), good aqueous solubility (>8.5 mg/mL at pH 5.2) which should facilitate formulation for iv administration, and excellent selectivity against the human arginine vasopressin receptors. Incorporation of a 5-fluoro substituent on the central benzoyl ring of this class of oxytocin antagonists enhanced in vitro and in vivo potency but was detrimental to the pharmacokinetic profiles of these compounds. Although lipophilic substitution around the pyridine ring of compound 30 gave higher affinity in vitro, such substituents were a metabolic liability and caused shortfalls in vivo. Two approaches to prevent this metabolism, addition of a cyclic constraint and incorporation of trifluoromethyl groups, were examined. The former approach was ineffective because of metabolic hydroxylation on the constrained ring system, whereas the latter showed improvement in plasma pharmacokinetics in some cases.
- Bell, Ian M.,Erb, Jill M.,Freidinger, Roger M.,Gallicchio, Steven N.,Guare, James P.,Guidotti, Maribeth T.,Halpin, Rita A.,Hobbs, Doug W.,Homnick, Carl F.,Kuo, Michelle S.,Lis, Edward V.,Mathre, David J.,Michelson, Stuart R.,Pawluczy, Joseph M.,Pettibone, Douglas J.,Reiss, Duane R.,Vickers, Stanley,Williams, Peter D.,Woyden, Carla J.
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p. 2146 - 2163
(2007/10/03)
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- Dopamine Autoreceptor Agonists as Potential Antipsychotics. 3. 6-Propyl-4,5,5a,6,7,8-hexahydrothiazoloquinolin-2-amine
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A series of rigid tricyclic analogues of the dopamine (DA) agonist PD 118440 was synthesized and evaluated for dopaminergic activity and DA autoreceptor selectivity. (R)-(+)-6-Propyl-4,5,5a,6,7,8-hexahydrothiazoloquinolin-2-amine ((+)-6) was identified as the most selective DA autoreceptor agonist from this group of compounds.It inhibited spontaneous locomotor activity (LMA) in rodents, reversed the γ-butyrolactone (GBL) induced accumulation of rat striatal DOPA and inhibited brain DA neuronal firing, all suggestive of direct DA autoreceptor agonist activity.However, (+)-6 is not completely free of postsynaptic DA activity, as evidenced by its stimulation of LMA in rats at high doses and its ability to produce stereotypy.On the other hand, (-)-6 appears to be a weak partial DA agonist with some effects on brain DA synthesis only at high doses.Like other DA autoreceptor agonists and DA antagonists, (+)-6 inhibited Sidman conditioned avoidance in squirrel monkeys, a test predictive of clinical antipsychotic activity.However, unlike classical antipsychotics, (+)-6 did not induce dystonias in haloperidol-sensitized squirrel monkeys, suggesting a minimal propensity toward extrapyramidal side effects (EPS).
- Caprathe, Bradley W.,Jaen, Juan C.,Wise, Lawrence D.,Heffner, Thomas G.,Pugsley, Thomas A.,et al.
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p. 2736 - 2746
(2007/10/02)
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