- Method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in continuous flow microreactor
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The invention relates to a method for synthesizing 4-(4-fluorobenzoyl) butyric acid and analogues thereof in a continuous flow microreactor, which comprises the following steps: (1) uniformly mixing a compound 1 and a compound 2 to obtain a homogeneous phase solution A; (2) uniformly mixing aluminum trichloride, a compound 1 and an organic solvent to obtain a homogeneous phase solution B; (3) diluting concentrated hydrochloric acid with water to prepare a solution C; and (4) transferring the homogeneous phase solution A and the homogeneous phase solution B into a first micro-reaction module for a Friedel-Crafts acylation reaction, after the reaction is finished, transferring the obtained reaction solution and the solution C into a second micro-reaction module for quenching reaction, and then performing liquid separation, washing and vacuum concentration to obtain a target compound 3; wherein the specific synthesis route is as follows. By adopting the method disclosed by the invention, the target product can be continuously and rapidly synthesized, aluminum trichloride is not needed for treatment, the reaction condition is mild, the reaction time is short, and the yield is high and reaches 90% or above.
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Paragraph 0065-0070
(2021/05/12)
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- Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters
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Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.
- Shi, Yongjie,Tan, Xuefeng,Gao, Shuang,Zhang, Yao,Wang, Jingxin,Zhang, Xumu,Yin, Qin
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supporting information
p. 2707 - 2713
(2020/03/30)
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- Asymmetric hydrogenation reaction γ - or δ - ketonato compound (by machine translation)
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The invention relates to the field, of organic chemistry, specifically γ - or δ - keto acid compound asymmetric hydrogenation reaction, reaction formula as follows : Wherein R is H,C. 1 - C6 An alkyl or halogen, is R 1 - 5 in number of substituents . wherein n is 1 or 2;Cat. is a chiral spiro pyrimidyl phosphine ligand iridium complex . and γ - or δ - keto acid compound is subjected to an internal esterification reaction to further prepare a lactone compound. (by machine translation)
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Paragraph 0048-0053
(2020/03/06)
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- Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones
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A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.
- Hua, Yun-Yu,Bin, Huai-Yu,Wei, Tao,Cheng, Hou-An,Lin, Zu-Peng,Fu, Xing-Feng,Li, Yuan-Qiang,Xie, Jian-Hua,Yan, Pu-Cha,Zhou, Qi-Lin
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supporting information
p. 818 - 822
(2020/02/15)
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- Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation
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A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
- Estopi?á-Durán, Susana,Donnelly, Liam J.,Mclean, Euan B.,Hockin, Bryony M.,Slawin, Alexandra M. Z.,Taylor, James E.
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supporting information
p. 3950 - 3956
(2019/02/16)
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- Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids
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A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.
- Duhamel, Thomas,Mu?iz, Kilian
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supporting information
p. 933 - 936
(2019/01/23)
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- Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
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Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
- Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
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supporting information
p. 16490 - 16494
(2019/11/03)
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- Iridium/f-Amphol-catalyzed Efficient Asymmetric Hydrogenation of Benzo-fused Cyclic Ketones
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Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%–99% yields, 93%–>99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093). (Figure presented.).
- Yin, Congcong,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 4319 - 4324
(2018/10/15)
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- Visible-Light-Promoted Metal-Free Aerobic Oxidation of Primary Amines to Acids and Lactones
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A unique metal-free aerobic oxidation of primary amines via visible light photocatalytic double carbon–carbon bonds cleavage and multi carbon–hydrogen bonds oxidation was observed. Aerobic oxidation of primary amines could be controlled to afford acids by using dioxane with 18 W CFL, and lactones by using DMF with 8 W green LEDs, respectively. A plausible mechanism was proposed based on control experiments. This observation showed direct evidences for the fragmentation in the aerobic oxidation of aliphatic primary amines.
- Cheng, Xiaokai,Yang, Bo,Hu, Xingen,Xu, Qing,Lu, Zhan
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supporting information
p. 17566 - 17570
(2016/11/29)
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- Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: Enantioselective synthesis of (+)-Centrolobine
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An efficient asymmetric hydrogenation of δ-keto Weinreb amides catalyzed by a Ru-Xyl-SunPhos-Daipen bifunctional catalyst has been achieved. This method afforded a series of enantio-enriched δ-hydroxy Weinreb amides in good yields (up to 93%) and enantioselectivities (up to 99%). This protocol was successfully applied to the synthesis of the key intermediate of (+)-Centrolobine.
- Zhao, Mengmeng,Lu, Bin,Ding, Guangni,Ren, Kai,Xie, Xiaomin,Zhang, Zhaoguo
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p. 2723 - 2730
(2016/03/05)
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- Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization
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A highly selective, controllable and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones has been achieved, affording N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported. Basic cyclizations: A highly selective, controllable, and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones affords N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize polycyclic aromatic compounds is also reported.
- Zhu, Chenghao,Qiu, Lin,Xu, Guangyang,Li, Jian,Sun, Jiangtao
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supporting information
p. 12871 - 12875
(2015/09/07)
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- Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3
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A simple and efficient method of Friedel-Crafts acylation of arenes with succinic anhydride, phthalic anhydride and glutaric anhydride under the action of 1-butyl-3-ethylimidazolium ([bmim]Br/AlCl3 ([bmim]+) cation (ionic liquid) and ultrasound irradiation is presented. Thy purity of products was tested by GC-MS and their structures evaluated by IR and 1H NMR spectroscopy.
- Fekri, Leila Zare,Nikpassand, Mohammad
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p. 1825 - 1829
(2015/01/09)
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- Electrochemical phenylselenoetherification as a key step in the synthesis of (±)-curcumene ether
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Two variants of a new pathway for the synthesis of (±)-curcumene ether are described. The key steps in these procedures are intramolecular cyclizations of 6-methyl-2-(4-methylphenyl)hept-6-en-2-ol and 2-methyl-6-(4-methylphenyl)hept-6-en-2-ol by means of an electrochemically generated phenylselenyl cation. This synthetic approach provides significantly better yields than the previously reported protocols. Copyright
- Stevanovic, Dragana,Pejovic, Anka,Damljanovic, Ivan S.,Vukicevic, Mirjana D.,Dobrikov, Georgi,Dimitrov, Vladimir,Denic, Marija S.,Radulovic, Niko S.,Vukicevic, Rastko D.
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p. 1103 - 1110
(2013/07/26)
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- NEW CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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- NEW CCR2 ANTAGONISTS
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) of formula (Ia) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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- NEW CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) of Formula (I) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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- NOVEL ANTAGONISTS FOR CCR2 AND USES THEREOF
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) of formula (I) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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- CCR2 RECEPTOR ANTAGONISTS
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The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.
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- Synthesis and anti-inflammatory activity of some 3-(4,6-disubtituted-2- thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) propanoic acid derivatives
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A series of 3-(4,6-disubtituted-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) propanoic acid derivatives has been synthesized by condensation of thiourea, 5-(4-subtituted phenyl)-5-oxopentanoic acid and substituted aldehyde. The synthesized compounds were screened for their anti-inflammatory activity using rat paw edema method. Most of the compounds from the series showed significant (p 0.05) anti-inflammatory activity.
- Mokale, Santosh N.,Shinde, Sandeep S.,Elgire, Rupali D.,Sangshetti, Jaiprakash N.,Shinde, Devanand B.
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experimental part
p. 4424 - 4426
(2010/09/09)
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- Hypervalent iodine(III) sulfonate mediated synthesis of 5-benzoyldihydro-2(3H)-furan-one in ionic solvent
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The room temperature ionic liquid, n-butylpyridinium tetrafluoroborate(BPyBF4) is used as a "green" recyclable solvent for the reaction of 4-benzoylbutyric acid with [hydroxy-(2,4-dinitrobenzenesulfonyloxy)iodo]-benzene (HDNIB) to prepare 5-benzoyldihydro-2(3H)-furanone.
- Hou, Rei-Sheu,Wang, Huey-Min,Lin, Yu-Chien,Chen, Ling-Chieg
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p. 649 - 656
(2007/10/03)
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