- Mild Cu-Catalyzed Oxidation of Benzylic Boronic Esters to Ketones
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The oxidation of benzylic boronic esters directly to the ketone is reported. This mild Cu-catalyzed method uses an ambient atmosphere of air as the terminal oxidant and is notably chemoselective. Oxidation of the C-B bond occurs selectively, even in the presence of unprotected alcohols. Initial investigation suggests the reaction proceeds through an alkylboron to Cu transmetalation, peroxide formation, and rearrangement to give the carbonyl.
- Grayson, James D.,Partridge, Benjamin M.
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p. 4296 - 4301
(2019/05/14)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Preparation method of quinoline derivative
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The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.
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Paragraph 0111; 0112
(2017/06/02)
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- Discovery and optimization of a series of imidazo[4,5-b]pyrazine derivatives as highly potent and exquisitely selective inhibitors of the mesenchymal–epithelial transition factor (c-Met) protein kinase
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Aberrant c-Met activation has been implicated in multiple tumor oncogenic processes and drug resistance. In this study, a series of imidazo[4,5-b]pyrazine derivatives was designed and synthesized, and their inhibitory activities were evaluated in vitro. Structure–activity relationship (SAR) was investigated systematically and docking analysis was performed to elucidate the binding mode, leading to the identification of the most promising compound 1D-2 which exhibited significant inhibitory effect on both enzymatic (IC50?=?1.45?nM) and cellular (IC50?=?24.7?nM in H1993 cell line) assays, as well as exquisite selectivity and satisfactory metabolic stability in human and rat liver microsomes.
- Zhao, Fei,Zhang, Jing,Zhang, Leduo,Hao, Yu,Shi, Chen,Xia, Guangxin,Yu, Jianxin,Liu, Yanjun
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p. 4281 - 4290
(2016/08/23)
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- Quinoline compounds and preparation method thereof, and intermediate, pharmaceutical composition and application of quinoline compounds
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The invention discloses quinoline compounds and a preparation method thereof, and an intermediate, a pharmaceutical composition and application of quinoline compounds. The invention provides quinoline compounds disclosed as Formula 1, and pharmaceutically acceptable salts, solvates, metabolites, metabolism precursors or pharmaceutical precursors thereof. The quinoline compounds have favorable inhibitory effects on tyrosine kinase C-Met, and can be used for preparing drugs for prevention, treatment or auxiliary treatment on multiple diseases related to C-Met expression or activity, and especially neoplastic diseases.
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- Quinoline and phenanthroline preparation starting from glycerol via improved microwave-assisted modified Skraup reaction
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An efficient "green" modified Skraup reaction in neat water was developed using inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions. Starting from aniline derivatives, various quinolines were obtained in 10-66% yields. The use of nitroaniline led to the corresponding phenanthrolines in 15-52% yields, respectively. This journal is the Partner Organisations 2014.
- Saggadi, Hanen,Luart, Denis,Thiebault, Nicolas,Polaert, Isabelle,Estel, Lionel,Len
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p. 21456 - 21464
(2014/06/10)
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- Lessons from (S)-6-(1-(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3- b ]pyridazin-3-yl)ethyl)quinoline (PF-04254644), an inhibitor of receptor tyrosine kinase c-met with high protein kinase selectivity but broad phosphodiesterase family inhibition lea
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The hepatocyte growth factor (HGF)/c-Met signaling axis is deregulated in many cancers and plays important roles in tumor invasive growth and metastasis. An exclusively selective c-Met inhibitor (S)-6-(1-(6-(1-methyl-1H-pyrazol-4-yl)- [1,2,4]triazolo[4,3-
- Cui, J. Jean,Shen, Hong,Tran-Dubé, Michelle,Nambu, Mitchell,McTigue, Michele,Grodsky, Neil,Ryan, Kevin,Yamazaki, Shinji,Aguirre, Shirley,Parker, Max,Li, Qiuhua,Zou, Helen,Christensen, James
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p. 6651 - 6665
(2013/10/01)
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- Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous Pd-C catalysis
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Nitroarenes having electron-donating or -withdrawing substituents are reduced to anilines and cyclized with tris(3- hydroxypropyl)amine in the presence of a catalytic amount of Pd-C along with tin(II) chloride and isopropanol in dioxane-H2O medium to give the corresponding quinolines in good to excellent yields. Copyright
- Cho, Chan Sik,Kim, Tae Gyun,Yoon, Nam Sik
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experimental part
p. 291 - 293
(2010/08/04)
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- IMIDAZO [1,2-B] PYRIDAZINE DERIVATIVES FOR THE TREATMENT OF C-MET TYROSINE KINASE MEDIATED DISEASE
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The invention relates to compounds of formula (I) and salts thereof, formula (I) wherein the substituents are as defined in the specification, the application of a compound of formula (I) in a process for the treatment of the human or animal body, in particular with regard to C-Met tyrosine kinase mediated disease; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharamaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner; processes for the preparation of a compound of formula (I).
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Page/Page column 77
(2009/10/21)
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- TRIAZOLOPYRAZINE DERIVATIVES
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The invention relates to compounds of the formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3 and R4 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formula I and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formula I.
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Page/Page column 40-41
(2008/06/13)
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- Ruthenium-Catalyzed Formation of Quinolines via Reductive Cyclization of Nitroarenes with Tris(3-hydroxypropyl)amine in an Aqueous Medium
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Nitroarenes react with tris(3-hydroxypropyl)amine in an aqueous medium (dioxane/H2O) at 180° in the presence of a catalytic amount of a ruthenium catalyst and tin(II) chloride along with isopropanol as hydrogen donor to afford the corresponding quinolines in good yields. The presence of tin(II) chloride is essential for the formation of quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from tris(3-hydroxypropyl)amine to anilines to form 3-anilino-l-propanols, N-alkylation of anilines by 3-anilino-1-propanol to form 1,3-dianilinopropane and intramolecular heteroannulation of 1, 3-dianilinopropane is proposed for this catalytic process.
- Cho, Chan Sik,Lee, Na Young,Choi, Heung-Jin,Kim, Tae-Jeong,Shim, Sang Chul
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p. 929 - 932
(2007/10/03)
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- Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols
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Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving i
- Cho, Chan Sik,Kyung Kim, Tae,Kim, Tae-Jeong,Shim, Sang Chul,Yoon, Nam Sik
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p. 291 - 294
(2007/10/03)
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- Tungstate-Catalyzed Oxidation of Tetrahydroquinolines with Hydrogen Peroxide: A Novel Method for the Synthesis of Cyclic Hydroxamic Acids
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The sodium tungstate catalyzed oxidation of 1,2,3,4-tetrahydroquinolines (1) with 30percent aqueous hydrogen peroxide solution in methanol gives 1-hydroxy-3,4-dihydroquinolin-2(1H)-ones (2), which are important biologically active compounds, in good to excellent yields.The cyclic hydroxamic acid 7 is also obtained in good yield.Since reduction of 2 thus obtained gives 3,4-dihydroquinolin-2(1H)-ones (4), the present reaction provides a convenient method for synthesis of 4 from 1.
- Murahashi, Shun-Ichi,Oda, Tetsuya,Sugahara, Toshiaki,Masui, Yoshiyuki
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p. 1744 - 1749
(2007/10/02)
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