- Controlled synthesis of 2-acetyl-6-carbethoxypyridine and 2,6-diacetylpyridine from 2,6-dimethylpyridine
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The controlled syntheses of mono- and bis-acetylpyridine from the same starting material (2,6-dimethylpyridine) are reported, including the asymmetrical compound 2-acetyl-6-carbethoxypyridine, which has not before been reported. The influences of the amount of catalyst EtONa and the reaction conditions to the final products are also explored. A modification of the reported preparation for the 2,6-dipicolinic acid, 2,6-dicarbethoxypyridine and 2,6-diacetylpyridine with higher purity and improved yields is provided here, and the physical and spectral properties of these products are identical to those reported in the literature. Copyright Taylor & Francis, Inc.
- Su, Biyun,Zhao, Jianshe,Cui, Yong,Liang, Yongqing,Sun, Wenhua
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- Copper ion fluorescence sensor molecules, preparation method, and application in detection of copper ions
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The invention discloses copper ion fluorescence sensor molecules, a preparation method, and application in detection of copper ions. The molecular chemical formula of a sensor is C29H35N7O4, and has the structure which is as shown in formula I; the preparation method of the copper ion fluorescence sensor molecules comprises the steps of taking 2,6-pyridinedicarboxylic acid as a raw material, chloridizing, performing hydrazinolysis and performing condensation reaction to obtain the sensor molecules. The prepared sensor molecules have high selectivity and sensitivity to the copper ions in a DMSOsolution, have obvious visual colorimetric response, and moreover, are not interfered with other cations. According to the preparation method, ion detection paper which is loaded with the sensor molecules is prepared and has the advantages of convenience in carrying, obvious phenomenon, rapid detection and the like. In addition, the fluorescence sensor molecules prepared by the preparation methodis simple in synthesis method and low in cost, and has a very good application prospect in the field of cationic detection.
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Page/Page column 7
(2019/08/26)
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- A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction
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An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).
- Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
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supporting information
p. 3031 - 3035
(2018/06/27)
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- Method for directly oxidizing benzyl-position C-H bond into ketone
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The invention discloses a method for directly oxidizing a benzyl-position C-H bond into ketone, wherein aryl ethyl compounds are catalyzed and oxidized by nitrite ester; a synergistic catalytic system of free radical initiator and nitrite ester is adopted, and a catalytic system of non-metallic catalyst and oxygen is adopted, the oxidization of the C-H bond of a free radical-activated aryl side chain is simple in operation; after completing the reaction, petroleum ether/ethyl acetate at a volume ratio of (50-1):1 is used as an eluent; column chromatography separation is performed to obtain a target product. The catalytic system in the invention uses oxygen as an oxygen source and has high atomic economy; the invention is a non-metallic catalytic system and provides a novel method for avoid metal residues in synthetic drugs; for diethyl aromatic hydrocarbon, the method provided by the invention can be adopted to selectively oxidize diethyl aromatic hydrocarbon into monoketone and diketone; the method of the invention can be adopted to efficiently synthesize tranquillizer lenperone, so that a novel method for synthesizing lenperone is provided.
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Paragraph 0120; 0121; 0124; 0125
(2017/08/29)
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- Organopromoted Selectivity-Switchable Synthesis of Polyketones
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In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.
- Liu, Jie,Hu, Kang-Fei,Qu, Jian-Ping,Kang, Yan-Biao
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supporting information
p. 5593 - 5596
(2017/10/25)
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- N ortho acyl substituted nitrogen-containing heterocyclic compound and process for preparing aminal iron (II) complexes thereof
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Provided are a process for preparing an N ortho acyl substituted nitrogen-containing heterocyclic compound and an aminal iron (II) complex thereof, and the use of the complexes obtained by the process in an olefin oligomerization catalyst. The N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is for example 2-acyl-1,10-phenanthroline or 2,6-diacetyl pyridine as shown in formula b, and the N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is produced by a reaction of a precursor thereof in a substituted or unsubstituted nitrobenzene. Preferably the precursor shown in formula I in the present invention is produced by 1,10-phenanthroline reacting with trialkyl aluminum, or a halogenoalkyl aluminum RnAIXm, or a substituted or unsubstituted benzyl lithium Ph′CH2Li, followed by hydrolysis. The preparation method provided in the present invention has a few synthetic steps, an easy process, a low toxic effect, and reduces the preparation costs of the catalyst, and has a promising outlook in the industrial application.
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Page/Page column 34
(2016/04/20)
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- New Type of 2,6-Bis(imidazo[1,2-a]pyridin-2-yl)pyridine-Based Ruthenium Complexes: Active Catalysts for Transfer Hydrogenation of Ketones
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Neutral and cationic ruthenium(II) complexes bearing a symmetrical 2,6-bis(imidazo[1,2-a]pyridin-2-yl)pyridine were synthesized and structurally characterized by NMR analysis and X-ray crystallographic determinations. These complexes have exhibited good catalytic activity in the transfer hydrogenation of ketones. In refluxing isopropyl alcohol, the conversion of the substrates reached up to 99%, and a TOF value of 356400 h-1 with 0.1 mol % catalyst was achieved. (Figure Presented).
- Li, Ke,Niu, Jun-Long,Yang, Ming-Ze,Li, Zhen,Wu, Li-Yuan,Hao, Xin-Qi,Song, Mao-Ping
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p. 1170 - 1176
(2015/04/27)
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- Sulfide oxidation by O2: Synthesis, structure and reactivity of novel sulfide-incorporated Fe(II) bis(imino)pyridine complexes
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The unsymmetrical iron(II) bis(imino)pyridine complexes [Fe II(LN3SMe)(H2O)3](OTf)2 (1), and [FeII(LN3-SMe)Cl2] (2) were synthesized and their reactivity with O2 was examined. Complexes 1 and 2 were characterized by single crystal X-ray crystallography, LDI-MS, 1H NMR and elemental analysis. The LN3SMe ligand was designed to incorporate a single sulfide donor and relies on the bis(imino)pyridine scaffold. This scaffold was selected for its ease of synthesis and its well-precedented ability to stabilize Fe(II) ions. Complexes 1 and 2 ware prepared via a metal-assisted template reaction from the unsymmetrical pyridyl ketone precursor 2-(O=CMe)-6-(2,6-(iPr 2-C6H3N=CMe)-C5H3N. Reaction of 1 with O2 was shown to afford the S-oxygenated sulfoxide complex [Fe(LN3S(O)Me)(OTf)]2+ (3), whereas compound 2, under the same reaction conditions, afforded the corresponding sulfone complex [Fe(LN3S(O2)Me)Cl]2+ (4).
- Widger, Leland R.,Siegler, Maxime A.,Goldberg, David P.
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p. 179 - 189
(2013/07/26)
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- A convenient approach for the synthesis of 2,6-diformyl- and 2,6-diacetylpyridines
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2,6-Diformyl- and 2,6-diacetylpyridines are readily accessed in good yields (60-90%) via the single-pot reaction of 2,6-pyridine dicarboxamides with LiAlH4 or MeMgCl in THF at 0-20°C. The high efficiency of the method illustrates the significance of solubility in the reduction and alkylation of difunctionalized substrates.
- Ivchenko, Pavel V.,Nifant'Ev, Ilya E.,Buslov, Ivan V.
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supporting information
p. 217 - 219
(2013/02/23)
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- Hydrosilylation Catalysts
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Disclosed herein are manganese, iron, cobalt, or nickel complexes containing terdentate pyridine diimine ligands and their use as efficient and selective hydrosilylation catalysts.
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- HYDROSILYLATION CATALYSTS
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Disclosed herein are manganese, iron, cobalt, or nickel complexes containing terdentate pyridine diimine ligands and their use as efficient and selective hydrosilylation catalysts.
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Page/Page column 19
(2011/02/24)
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- Novel late transition metal catalysts based on iron: Synthesis, structures and ethylene polymerization
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In this article we reported synthesis, characterization and ethylene polymerization behavior of two new late transition metal 2,6-bis(imino)pyridine catalysts based on iron(II) possessing different substituents of NO2 (catalyst b) and OMe (catalyst c) at the para position of the pyridine ring. Theoretical study exhibited more positive charge on the central metal of the catalyst b, leading to higher activity offset by lower thermal stability and life time.
- Zohuri, Gholam Hossein,Seyedi, Seyed Mohammad,Sandaroos, Reza,Damavandi, Saman,Mohammadi, Ali
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scheme or table
p. 160 - 166
(2011/10/03)
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- Asymmetric synthesis catalyzed by transition metal complexes with new chiral ligands
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A chiral ligand having the following structure: STR1 wherein AR is any aromatic and/or ring structure, and R is selected from the group consisting of aryl, oxygenated aryl, alkyl, oxygenated alkyl, AR, oxygenated AR and combinations thereof.
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- Synthesis of (1R, 1R')-2,6-bis[1-(diphenylphosphino)ethyl]pyridine and its application in asymmetric transfer hydrogenation
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A C2 symmetric tridentate ligand, (1R, 1R') 2,6-Bis[1-(diphenylphosphino)ethyl]pyridine, has been synthesized in enantiomerically pure form. A practical method to synthesize a variety of chiral pyridyl diols is reported. Asymmetric transfer hydrogenation is achieved using the tridentate ligand.
- Jiang,Van Plew,Murtuza,Zhang
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p. 797 - 800
(2007/10/03)
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- Simple and mild method for preparation of α-pyridinecarboxylates and α-pyridyl ketones via trimethylstannyl derivatives
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Alkoxycarbonylation and acylation at the α-position of pyridine, quinoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions.
- Yamamoto,Ouchi,Tanaka
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p. 1028 - 1030
(2007/10/03)
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