- Zn(OTf)2-catalyzed reactions of ethenetricarboxylates with 2-aminobenzaldehydes leading to tetrahydroquinoline derivatives
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(Graph Presented) Quinolines are an important class of compounds, and the development of new efficient synthetic strategies for the construction of quinolines is of considerable interest. Zinc triflate catalyzed cyclization of ethenetricarboxylate derivat
- Yamazaki, Shoko,Takebayashi, Masachika,Miyazaki, Kazuya
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Read Online
- Compound serving as thyroid hormone beta receptor agonist and use thereof
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The invention relates to a compound serving as a thyroid hormone beta receptor agonist and use thereof, and further relates to a pharmaceutical composition containing the compound. The compound or thepharmaceutical composition can be used for preparing a
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Paragraph 0338-0342
(2021/02/10)
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- Construction of a benzo[b]azepine skeleton through decarboxylative ylide [6+1] annulations with modified vinyl benzoxazinanones
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A Lewis acid-promoted [6+1] annulation between sulfur ylides and modified vinyl benzoxazinanones was described. In this reaction, the newly designed vinyl benzoxazinanones could serve as a novel six-atom synthon, and the key to success is the installation of an electron-withdrawing group on the alkene moiety of the benzoxazinanones. A broad range of substrates are compatible with this mild reaction system, thereby providing a facile and practical approach for constructing a benzo[b]azepine skeleton.
- Li, Qing-Zhu,Jia, Zhi-Qiang,Chen, Lin,Zhang, Xiang,Leng, Hai-Jun,Zeng, Rong,Liu, Yan-Qing,Zou, Wen-Lin,Li, Jun-Long
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supporting information
p. 814 - 818
(2021/02/16)
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- Access to 5,6-Spirocycles Bearing Three Contiguous Stereocenters via Pd-Catalyzed Stereoselective [4 + 2] Cycloaddition of Azadienes
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We present herein a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones, which represents a rare highly stereoselective cycloaddition of this class of fused azadienes as a two-atom synthon. The use of a phosphoramidite ligand bearing a chiral secondary amine with a simple biphenyl backbone proved to be the key to construct the novel spirocyclic tetrahydroquinoline scaffold containing three contiguous stereocenters as a single diastereomer in high enantioselectivity.
- Fairuz Binte Sheikh Ismail, Siti Nur,Yang, Binmiao,Zhao, Yu
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supporting information
p. 2884 - 2889
(2021/05/05)
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- Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
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α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.
- Li, Ling,Zhang, Shiqi,Deng, Xiongfei,Li, Guangxun,Tang, Zhuo,Zhao, Gang
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supporting information
p. 6819 - 6824
(2021/09/08)
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- A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines
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The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.
- Wang, Xinyue,Li, Zefei,Feng, Chang,Zhen, Qi,Guo, Mingzhang,Yao, Yaning,Zou, Xinyu,Wang, Pengfei,Hou, Yunlei,Gong, Ping
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supporting information
p. 2090 - 2096
(2021/09/06)
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- PNO ligand containing planar chiral ferrocene and application thereof
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The invention discloses a PNO ligand containing planar chiral ferrocene and application thereof. The PNO ligand containing planar chiral ferrocene is a planar chiral ferrocene-containing and phenol-containing PNO ligand as shown in a general formula (I) or (II) which is described in the specification, or a planar chiral ferrocene-containing and aryl-phosphoric-acid-containingPNO ligand containing as shown in a general formula (III) or (IV) which is described in the specification, or a planar chiral ferrocene-containing and carbon-chiral-phenol-containingPNO ligand as shown in a general formula (V) or (VI) which is described in the specification. The invention provides tridentate PNO ligands and processes for their complexation with transition metal salts or transition metal complexes; the introduction of salicylaldehyde and derivatives thereof, which are simple and easy to obtain, enables the ligands to have a bifunctionalization effect, and -OH in a formed catalyst has stronger acidity and is beneficial to combination with N/O in polar double bonds. Therefore, due to the bifunctionalization effect of the catalyst, the interaction between the catalyst and a substrate can be greatly improved, so a reaction can obtain higher catalytic activity and stereoselectivity.
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Paragraph 0114-0118
(2021/06/21)
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- Red phosphorescence compound and organic electroluminescence device using same
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The invention discloses a red phosphorescence compound, and an organic electroluminescence device using same; in the organic electroluminescence device comprising, in a successive deposition manner, apositive electrode, a hole injection layer, a hole transfer layer, a luminescent layer, an electron transmission layer, an electron injection layer, and a negative electrode, a phosphorescence compound, represented as the formula (I), can be employed as the doping agent for the luminescent layer, wherein the R1 to R5 are independently selected from one of H, C1-C6 alkyl group, and C5-C8 cycloalkyl group, and X comprises a trialkylmonosilane structure. The red phosphorescence compound has high efficiency, high color purity and narrow spectrum.
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Paragraph 0050-0052
(2020/03/17)
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- Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines
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In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.
- Chen, Yang-Bo,Sun, Zhou,Wang, Ze-Shu,Ye, Long-Wu,Zhang, Hao-Wen,Zhu, Chunyin
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supporting information
p. 3636 - 3644
(2020/03/06)
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- One-pot synthesis of 2-hydroxymethylindoles: via photoredox-catalyzed ketyl-ynamide coupling/1,3-allylic alcohol transposition
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An efficient visible-light-mediated ketyl-ynamide coupling by employing ynamides bearing alkyl sulfonyl substituents to deliver eneindolin-3-ols has been developed. Subsequent 1,3-transposition of allylic alcohols in one pot is capable of synthesizing 2-hydroxymethylindoles in generally moderate to good yields. The synthetic utility of this protocol has also been demonstrated by the facile and practical synthesis of two bioactive molecules. The use of readily available substrates, a simple procedure and benign reaction conditions render this method a viable alternative for the synthesis of 2-hydroxymethylindoles. This journal is
- Chen, Yang-Bo,Wang, Kun,Wang, Ze-Shu,Xu, Zhou,Ye, Long-Wu
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supporting information
p. 4483 - 4488
(2020/08/10)
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- Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives
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Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is
- Zhang, Jingjing,Xu, Wentao,Qu, Yi,Liu, Yuxiu,Li, Yongqiang,Song, Hongjian,Wang, Qingmin
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supporting information
p. 15212 - 15215
(2020/12/21)
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- A Paramagnetic NMR Spectroscopy Toolbox for the Characterisation of Paramagnetic/Spin-Crossover Coordination Complexes and Metal–Organic Cages
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The large paramagnetic shifts and short relaxation times resulting from the presence of a paramagnetic centre complicate NMR data acquisition and interpretation in solution. As a result, NMR analysis of paramagnetic complexes is limited in comparison to diamagnetic compounds and often relies on theoretical models. We report a toolbox of 1D (1H, proton-coupled 13C, selective 1H-decoupling 13C, steady-state NOE) and 2D (COSY, NOESY, HMQC) paramagnetic NMR methods that enables unprecedented structural characterisation and in some cases, provides more structural information than would be observable for a diamagnetic analogue. We demonstrate the toolbox's broad versatility for fields from coordination chemistry and spin-crossover complexes to supramolecular chemistry through the characterisation of CoII and high-spin FeII mononuclear complexes as well as a Co4L6 cage.
- Lehr, Marc,McConnell, Anna J.,N?ther, Christian,Paschelke, Tobias,S?nnichsen, Frank D.,Trumpf, Eicke,Vogt, Anna-Marlene
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supporting information
p. 19344 - 19351
(2020/09/01)
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- Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
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Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
- Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
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supporting information
p. 4703 - 4708
(2019/06/27)
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- Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
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A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.
- Vinoth, Perumal,Karuppasamy, Muthu,Vachan,Muthukrishnan, Isravel,Maheswari, C. Uma,Nagarajan, Subbiah,Pace, Vittorio,Roller, Alexander,Bhuvanesh, Nattamai,Sridharan, Vellaisamy
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- Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade
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An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
- Karuppasamy, Muthu,Vachan,Vinoth, Perumal,Muthukrishnan, Isravel,Nagarajan, Subbiah,Ielo, Laura,Pace, Vittorio,Banik, Subrata,Maheswari, C. Uma,Sridharan, Vellaisamy
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p. 5784 - 5788
(2019/08/26)
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- Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines
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The first enantioselective sequential phosphine-catalyzed (SPC as abbreviation) mode for the formation of tetrahydroquinolines with an ethynyl-substituted all-carbon quaternary stereogenic center is reported. In this SPC process, a novel [4 + 2] annulation process was devised employing α-substituted allenoates as C2 synthons (α-β′, 1,2-dipole) for the first time. 3-Ethynyl-substituted tetrahydroquinolines were readily prepared in good yields and high enantioselectivities.
- Zhang, Qinglong,Jin, Hongxing,Feng, Jiaxu,Zhu, Yannan,Jia, Penghao,Wu, Chengzhou,Huang, You
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supporting information
p. 1407 - 1411
(2019/03/07)
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- Discovery and Optimization of Novel Hydrogen Peroxide Activated Aromatic Nitrogen Mustard Derivatives as Highly Potent Anticancer Agents
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We describe several new aromatic nitrogen mustards with various aromatic substituents and boronic esters that can be activated with H2O2 to efficiently cross-link DNA. In vitro studies demonstrated the anticancer potential of these compounds at lower concentrations than those of other clinically used chemotherapeutics, such as melphalan and chlorambucil. In particular, compound 10, bearing an amino acid ester chain, is selectively cytotoxic toward breast cancer and leukemia cells that have inherently high levels of reactive oxygen species. Importantly, 10 was 10-14-fold more efficacious than melphalan and chlorambucil for triple-negative breast-cancer (TNBC) cells. Similarly, 10 is more toxic toward primary chronic-lymphocytic-leukemia cells than either chlorambucil or the lead compound, 9. The introduction of an amino acid side chain improved the solubility and permeability of 10. Furthermore, 10 inhibited the growth of TNBC tumors in xenografted mice without obvious signs of general toxicity, making this compound an ideal drug candidate for clinical development.
- Chen, Wenbing,Fan, Heli,Balakrishnan, Kumudha,Wang, Yibin,Sun, Huabing,Fan, Yukai,Gandhi, Varsha,Arnold, Leggy A.,Peng, Xiaohua
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p. 9132 - 9145
(2018/10/20)
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- 6 - Substituted pyridine agents ketone compound and use thereof
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The invention discloses a 6-substituted pyridyl quinazolinone compound with a novel structure. The structure of the compound is shown in formula I in the description, wherein in the formula I, L is selected from L1 or L2; R1 is selected from hydrogen, C1-
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Paragraph 0123; 0124; 0125
(2018/06/21)
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- Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles
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A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
- Cao, Bo,Simaan, Marwan,Marek, Ilan,Wei, Yin,Shi, Min
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supporting information
p. 216 - 219
(2016/12/27)
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- Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization
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The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This rea
- Mei, Guang-Jian,Bian, Chen-Yu,Li, Guo-Hao,Xu, Shao-Li,Zheng, Wen-Qin,Shi, Feng
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supporting information
p. 3219 - 3222
(2017/06/23)
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- Deuterium kinase selective inhibitor
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The invention relates to a deuterium kinase selective inhibitor and provides a compound shown as formula (I), a stereoisomer, a tautomer or pharmaceutically acceptable salt thereof and the application of the compound used as FGFR4 kinase selective inhibit
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Paragraph 0061; 0064
(2017/11/30)
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- Pd(II)-catalyzed enantioselective intramolecular oxidative amination utilizing (+)-camphorsulfonic acid
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An enantioselective Pd(II)-catalyzed intramolecular oxidative amination reaction was developed utilizing the commercially available chiral X-type ligand (1S)-(+)-camphorsulfonic acid. The Wacker-type cyclization produced chiral indoline products with enantioselectivies up to 45% ee. Electronic structure calculations employing density functional theory support a trans-aminopalladation mechanism.
- Aebly, Andrew H.,Rainey, Trevor J.
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supporting information
p. 3795 - 3799
(2017/09/15)
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- Lewis Acid-Catalyzed C(sp3)–C(sp3) Bond Forming Cyclization Reactions for the Synthesis of Tetrahydroprotoberberine Derivatives
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An efficient Lewis acid-catalyzed C(sp3)–C(sp3) bond forming annulation reaction has been developed. This strategy serves as a new method for the facile synthesis of tetrahydro-5H-isoquinolino[2,1-g][1,6]naphthyridine derivatives. A wide range of 2-methylquinoline-3-carbaldehydes and 1,2,3,4-tetrahydroisoquinolines can be applied for this process to afford structurally diverse tetrahydroprotoberberine derivatives in excellent yields. (Figure presented.).
- Li, Jianjun,Qin, Cong,Yu, Yang,Fan, Huaqiang,Fu, Yiwei,Li, Hao,Wang, Wei
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supporting information
p. 2191 - 2195
(2017/07/07)
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- Inhibitors of the fibroblast growth factor receptor
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Described herein are inhibitors of FGFR-4, pharmaceutical compositions including such compounds, and methods of using such compounds and compositions to inhibit the activity of FGFR-4.
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Page/Page column 37; 38
(2017/08/01)
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- Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid
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A catalytic asymmetric method for the synthesis of chiral isoquinolinonaphthyridines has been developed. A chiral disulfonimide catalyzes a redox cyclization reaction between 2-methyl-3-aldehydeazaarenes and 1,2,3,4-tetrahydroisoquinolines to deliver a range of isoquinolinonaphthyridines with good to high yields (up to 91%) and up to 92:8 er.
- Li, Jianjun,Fu, Yiwei,Qin, Cong,Yu, Yang,Li, Hao,Wang, Wei
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supporting information
p. 6474 - 6477
(2017/08/16)
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- Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines
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A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene to afford (Z)-phenyl-2-styrylquinolines, phenylnaphthyridine, and alkyne-substituted quinolines, respectively. The proposed mechanism and significant role of the solvent were well supported by isolating the azadiene intermediate and deuterium-labeling studies.
- Saunthwal, Rakesh K.,Patel, Monika,Verma, Akhilesh K.
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supporting information
p. 2200 - 2203
(2016/06/01)
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- Sunlight-Driven Forging of Amide/Ester Bonds from Three Independent Components: An Approach to Carbamates
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A photoredox catalytic route to carbamates enabled by visible irradiation (or simply sunlight) has been developed. This process leads to a novel approach to the construction of heterocyclic rings wherein the amide or ester motifs of carbamates were assembled from three isolated components. Large-scale experiments were realized by employing continuous flow techniques, and reuse of photocatalyst demonstrated the green and sustainable aspects of this method.
- Zhao, Yating,Huang, Binbin,Yang, Chao,Chen, Qingqing,Xia, Wujiong
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supporting information
p. 5572 - 5575
(2016/11/17)
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- 6-substituted pyrimidyl quinazolinone compound and application thereof
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The invention discloses a 6-substituted pyrimidyl quinazolinone compound having a novel structure represented as the general formula (I) and a salt thereof, wherein the substituent groups in the formula are defined as the specification. The compound has excellent insecticidal activity and can be used for preventing and treating insect pests in agriculture, forestry or non-treatment target, especially, the application for preventing and treating aphids.
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Paragraph 0111; 0112; 0113
(2016/10/09)
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- INHIBITORS OF THE FIBROBLAST GROWTH FACTOR RECEPTOR
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Described herein are inhibitors of FGFR-4, pharmaceutical compositions including such compounds, and methods of using such compounds and compositions to inhibit the activity of FGFR-4.
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Paragraph 0125; 0216
(2015/07/22)
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- Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides
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Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Bronsted base, respectively.
- Zhan, Gu,Shi, Ming-Lin,He, Qing,Du, Wei,Chen, Ying-Chun
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supporting information
p. 4750 - 4753
(2015/10/12)
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- Heteroatom insertion into 3,4-dihydro-1 H-quinolin-2-ones leads to potent and selective inhibitors of human and rat aldosterone synthase
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Aldosterone synthase (CYP11B2) catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone. CYP11B2 is regarded as a new target for several cardiovascular diseases which are associated with chronically elevated aldosterone levels such as hypertension, congestive heart failure and myocardial fibrosis. In this paper, we optimized heterocycle substituted 3,4-dihydropyridin-2(1H)-ones as CYP11B inhibitors by systematic introduction of heteroatoms and by bioisosteric exchange of the lactame moiety by a sultame moiety. The most promising compounds regarding inhibition of human CYP11B2 and selectivity versus human enzymes CYP11B1, CYP17, and CYP19 were tested for inhibition of rat CYP11B2. Thus, we discovered compounds 4 and 9 which show potent inhibition of hCYP11B2 (IC50 1 nM) and the corresponding rat enzyme (4: 64%, 9: 51% inhibition, at 2. 2 μM).
- Grombein, Cornelia M.,Hu, Qingzhong,Rau, Sabrina,Zimmer, Christina,Hartmann, Rolf W.
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p. 788 - 796
(2015/02/19)
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- INHIBITORS OF THE FIBROBLAST GROWTH FACTOR RECEPTOR
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Described herein are inhibitors of FGFR, pharmaceutical compositions including such compounds, and methods of using such compounds and compositions to inhibit the activity of tyrosine kinases.
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Page/Page column 37
(2014/02/15)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 5114 - 5121
(2014/07/08)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 5114 - 5121
(2014/12/10)
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- One-pot catalytic enantioselective synthesis of functionalized tetrahydroquinolines by aza-michael/michael cascade reactions of N-protected 2-aminophenyl α,β-unsaturated esters with Nitroolefins
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A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).
- Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 3365 - 3373
(2015/01/09)
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- Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via suzuki coupling provide access to complex polyheterocyclic biaryls
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Modular preassembly of azaxylylene photoprecursors, halogen-substituted in the aromatic ring, their intramolecular [4 + 4] or [4 + 2] cycloadditions to tethered unsaturated pendants, and subsequent postphotochemical capstone modification of the primary photoproducts via Suzuki coupling provides rapid access to diverse biaryls of unprecedented topology. This synthetic sequence allows for rapid growth of molecular complexity and is well aligned with methodology of Diversity-Oriented Synthesis.
- Cronk, W. Cole,Mukhina, Olga A.,Kutateladze, Andrei G.
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p. 1235 - 1246
(2014/03/21)
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- N-heterocyclic carbene-catalyzed enantioselective intramolecular N-tethered aldehyde-ketone benzoin reactions
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The N-heterocyclic carbene-catalyzed enantioselective intramolecular benzoin reaction of N-tethered substrates was realized. With 15 mol % of d-camphor-derived triazolium salt E and 10 mol % of NaOAc, the aldehyde-ketone cross benzoin reactions of various substituted N-tethered substrates proceeded smoothly to afford dihydroquinolinone derivatives with a quaternary carbon stereocenter in moderate to good yields and excellent ee.
- Jia, Min-Qiang,You, Shu-Li
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supporting information
p. 622 - 624
(2013/05/09)
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- Gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amines: An expedient route to 3-aminoquinolines
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Access to aminoquinolines: A gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amine was studied. The study provided, for the first time, direct access to 3-aminoquinolines in one step starting from readily available starting materials (see scheme). Elegantly designed experiments were employed to unravel the mechanism of this unprecedented rearrangement, which are corroborated by DFT calculations.
- Patil, Nitin T.,Raut, Vivek S.,Shinde, Valmik S.,Gayatri, Gaddamanugu,Sastry, G. Narahari
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supporting information; experimental part
p. 5530 - 5535
(2012/05/21)
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- A concise and cascade synthesis of batracylin and substituted isoindolo-[1,2- b ]quinazolin-12(10 H)-ones
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A concise, highly convergent, and practical synthesis of the clinical-phase anticancer agent batracylin in a two-stage process in excellent yield is described. The B and C rings of this tetracyclic heterocycle are constructed by cascade cyclization of 5-nitro-2-aminobenzyl alcohol with 2-cyanomethyl benzoate in trifluoroacetic acid in good yield in a single-pot reaction. A plausible mechanism for the cascade reaction is also proposed. As part of these studies, a range of batracylin derivatives with different substituents on the C and D rings are synthesized. Georg Thieme Verlag Stuttgart.
- Shankar,Wagh, Manoj Balu,Madhubabu,Vembu,Kumar, U. K. Syam
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supporting information; experimental part
p. 844 - 848
(2011/06/21)
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- Inhibitors of the Human Aldosterone Sythase CYP11B2
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The invention provides compounds of the general formula (I) which are inhibitors of the human aldosterone synthase, and also pharmaceutical compositions containing these compounds, and a method of treating of hyperaldosteronism and/or disorders or diseases that are mediated by 11β-hydroxylase (CYP11B1) with these compounds.
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Page/Page column 33; 34
(2011/05/16)
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- PYRIMIDONE DERIVATIVES USED AS TAU PROTEIN KINASE 1 INHIBITORS
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A compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: wherein Z represents nitrogen atom or C-X; X represents hydrogen atom or fluorine atom; R1 is hydrogen atom or a C1 -C3 alkyl group; L represents single bond or a C1 -C6 alkylene group which may be substituted; Y represents single bond, sulfur atom, oxygen atom, NH, or the like; R2 represents hydrogen atom or a cyclic group which may be substituted, which is used for preventive and/or therapeutic treatment of a disease caused by abnormal activity of tau protein kinase 1 such as a neurodegenerative diseases (e.g. Alzheimer disease).
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Page/Page column 47-48
(2011/02/24)
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- Design, synthesis, and in vitro pharmacology of new radiolabeled γ-hydroxybutyric acid analogues including photolabile analogues with irreversible binding to the high-affinity γ-hydroxybutyric acid binding sites
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γ-Hydroxybutyric acid (GHB) is a psychotropic compound endogenous to the brain. Despite its potential physiological significance, the complete molecular mechanisms of action remain unexplained. To facilitate the isolation and identification of the high-affinity GHB binding site, we herein report the design and synthesis of the first 125I-labeled radioligands in the field, one of which contains a photoaffinity label which enables it to bind irreversibly to the high-affinity GHB binding sites.
- Sabbatini, Paola,Wellendorph, Petrine,H?g, Signe,Pedersen, Martin H. F.,Br?uner-Osborne, Hans,Martiny, Lars,Fr?lund, Bente,Clausen, Rasmus P.
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supporting information; experimental part
p. 6506 - 6510
(2010/11/18)
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- Diphosphine-catalyzed mixed double-michael reaction: A unified synthesis of lndolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1- oxazines
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(Figure Presented) Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridlnes, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinuc
- Sriramurthy, Vardhineedi,Kwon, Ohyun
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supporting information; experimental part
p. 1084 - 1087
(2010/06/15)
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- GLYCINE B ANTAGONISTS
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The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.
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Page/Page column 45
(2010/04/27)
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- 6-PYRIDIN-3-YL-3,4-DIHYDRO-1H-QUINOLIN-2-ONE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE HUMAN ALDOSTERONE SYNTHASE CYP11B2
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The invention provides compounds of the general formula (I) which are inhibitors of the human aldosterone synthase, and also pharmaceutical compositions containing these compounds, and the use of these compounds and other heteroaryl substituted quinolinone derivatives for the treatment of hyperaldosteronism and/or disorders or diseases that are mediated by 11 β-hydroxylase (CYP11 B1 ).
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Page/Page column 51
(2010/01/29)
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- COMPOUNDS 947
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A compound of formula (I) or a pharmaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, for example in the treatment of proliferative disease such as cancer and partic
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Page/Page column 108
(2009/03/07)
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- Substituent effects upon the catalytic activity of aromatic cyclic seleninate esters and spirodioxyselenuranes that act as glutathione peroxidase mimetics
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(Chemical Equation Presented) Substituent effects were studied in a series of aromatic cyclic seleninate esters and spirodioxyselenuranes that function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. The methoxy-substituted selenurane proved the most efficacious catalyst for the reduction of hydrogen peroxide with benzyl thiol, and the reaction rates were enhanced for both classes by electron-donating substituents. Hammett plots indicated ρ = -0.45 and -3.1 for the seleninates and selenuranes, respectively, suggesting that oxidation at Se is the rate-determining step in their catalytic cycles.
- Press, David J.,Mercier, Eric A.,Kuzma, Dusan,Back, Thomas G.
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p. 4252 - 4255
(2008/09/20)
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- COMPOSITIONS AND METHODS FOR MODULATING GATED ION CHANNELS
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The alleged invention relates to indole derivatives according to formula 1, namely, wherein X is CH2, O, NR2 or NOR2 and wherein A is preferably a six membered ring involving a nitrogen heteroatom. These compounds and their pharmaceutical acceptable salts are used for modulating gated ion channels in order to treat pain, inflammatory disorders, neurological disorders, or diseases associated with the genitourinary or gastrointestinal systems.
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Page/Page column 136
(2008/06/13)
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- MACROLONE COMPOUNDS
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A compound of formula (I) compositions comprising same, processes for their preparation and use of said compounds, particularly in the treatment of microbial infections.
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Page/Page column 59-60
(2008/06/13)
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