- Unexpected Sole Enol-Form Emission of 2-(2′-Hydroxyphenyl)oxazoles for Highly Efficient Deep-Blue-Emitting Organic Electroluminescent Devices
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Considerable efforts have been devoted to the development of highly efficient blue light-emitting materials. However, deep-blue fluorescence materials that can satisfy the Commission Internationale de l'Eclairage (CIE) coordinates of (0.14, 0.08) of the N
- Li, Bijin,Tang, Guoqiang,Zhou, Linsen,Wu, Di,Lan, Jingbo,Zhou, Liang,Lu, Zhiyun,You, Jingsong
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Read Online
- Determination of band edges and their influences on photocatalytic reduction of nitrobenzene by bulk and exfoliated g-C3N4
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Thermally and chemically exfoliated metal-free semiconducting g-C3N4 are synthesized from bulk g-C3N4. Thorough characterization of the synthesized materials is performed with the help of XRD, FTIR, FE-SEM, PL, surface area analysis and DRS to probe differences in structural, morphological and optical properties between thermally and chemically exfoliated g-C3N4. The synthesized materials are exposed to light for photocatalytic reduction of nitrobenzene. The complete reduction reaction mechanism and product selectivity over the synthesized catalysts are studied in this report. The rate of reduction of nitrobenzene is found to be higher with thermally exfoliated g-C3N4, and the selectivity of aniline is found to be higher in the case of chemical exfoliated g-C3N4. The differences in the reactivity are explained in terms of structure, surface morphologies and band edge positions.
- Challagulla, Swapna,Payra, Soumitra,Chakraborty, Chanchal,Roy, Sounak
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Read Online
- Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study
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ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted
- Wang, Yi,Chen, Xiaoli,Lin, Shuang,Gao, Hui,Liu, Fu-Xiaomin,Zhou, Zhi,Yi, Wei
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supporting information
(2022/01/08)
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- Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization
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The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.
- Korch, Katerina M.,Watson, Donald A.
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supporting information
p. 7285 - 7289
(2021/09/14)
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- An Activity-Based Sensing Fluorogenic Probe for Monitoring Ethylene in Living Cells and Plants
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Ethylene (ET) is an important gaseous plant hormone. It is highly desirable to develop fluorescent probes for monitoring ethylene in living cells. We report an efficient RhIII-catalysed coupling of N-phenoxyacetamides to ethylene in the presenc
- Chen, Yiliang,Guo, Duojing,Jing, Maofeng,Li, Ji,Li, Yu,Liu, Hao,Wang, Biao,Wei, Lirong,Yan, Wei,Ye, Yonghao,Yu, Na,Zhao, Jing,Zheng, Ying
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supporting information
p. 21934 - 21942
(2021/08/30)
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- Synthesis of ortho-phenolic sulfilimines via an intermolecular sulfur atom transfer cascade reaction
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To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.
- Ren, Yan,Song, Yinan,Xiong, Feng,Xu, Shaojian,Zhang, Linxing,Zhang, Xinhao,Zuo, Yingying
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p. 3799 - 3803
(2020/06/08)
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- Rhodium(III)-Catalyzed Enantio- and Diastereoselective C?H Cyclopropylation of N-Phenoxylsulfonamides: Combined Experimental and Computational Studies
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Cyclopropane rings are a prominent structural motif in biologically active molecules. Enantio- and diastereoselective construction of cyclopropanes through C?H activation of arenes and coupling with readily available cyclopropenes is highly appealing but
- Zheng, Guangfan,Zhou, Zhi,Zhu, Guoxun,Zhai, Shuailei,Xu, Huiying,Duan, Xujing,Yi, Wei,Li, Xingwei
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supporting information
p. 2890 - 2896
(2020/01/24)
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- Pyrazole formaldoxime ether compound as well as preparation method and application thereof
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The invention discloses a pyrazole formaldoxime ether compound as well as a preparation method and application thereof. The structural formula of the pyrazole formaldoxime ether compound is shown as the following formula I shown in the specification, wherein in the formula I, R1 represents at least one of hydrogen, C1-C6 alkyl, C1-C6 alkyl monosubstituted by halogen and C1-C6 alkyl polysubstitutedby halogen; R2 represents at least one of hydrogen, C1-C6 alkyl, C1-C6 alkyl monosubstituted or polysubstituted by halogen, aryl and substituted aryl; R3 represents at least one of phenyl, benzyl, substituted benzyl, substituted phenyl, an unsubstituted nitrogen and/or oxygen-containing heterocyclic group, a substituted nitrogen and/or oxygen-containing heterocyclic group, an unsubstituted C3-C8cycloalkyl group and a substituted C3-C8 cycloalkyl group. The pyrazole formaldoxime ether compound takes oxime ether as a main skeleton structure, is simple in preparation method, can be used for efficiently preventing and treating fungal diseases and oomycete diseases of farmland crops, and can be used for disease resistance management.
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Paragraph 0055-0057
(2020/09/09)
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- Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C-H/C-C Activations
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A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C-H/C-C activations using internal oxidative O-NHAc and -OH as the dual directing groups has been achieved. This reaction provided an efficient and regioselective approach to benzofuran derivatives with good functional group compatibility and high yields.
- Pan, Jin-Long,Liu, Chang,Chen, Chao,Liu, Tuan-Qing,Wang, Man,Sun, Zhenliang,Zhang, Shu-Yu
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p. 2823 - 2827
(2019/04/30)
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- An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation
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Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C–S bond-forming methods. However, a mild, transition-metal-free, direct C–H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions.
- Zuo, Yingying,Xiong, Feng,Zhao, Jing
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p. 4174 - 4179
(2019/05/24)
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- RhIII-Catalyzed Decarboxylative o-Acylation of Arenes Bearing an Oxidizing Directing Group
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Here in we report, rhodium(III)-catalyzed decarboxylative acylation of arenes using α-oxocarboxylic acids as acyl surrogate. In this strategy, O–NHAc group act as an autocleavable oxidizing directing group (ODGauto), thus giving rise to ortho-acylated phenols in moderate to good yields. Mechanistic studies provided strong support for a kinetically relevant C–H bond activation. According to the best of our knowledge, this is the first report of Rhodium catalyzed decarboxylative acylation.
- Bera, Suvankar,Chandrasekhar,Chatterjee, Satadru,Killi, Sunil Kumar,Sarkar, Debabrata,Banerji, Biswadip
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p. 3877 - 3881
(2019/06/28)
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- Synthesis of Benzofurans and Benzoxazoles through a [3,3]-Sigmatropic Rearrangement: O-NHAc as a Multitasking Functional Group
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The synthesis of heterocycles relies heavily on diverse sigmatropic rearrangements triggered by the cleavage of X-Y (X, Y = C, O, N, S, I) bonds. However, a unified rearrangement approach for constructing heterocyclic libraries is highly desirable. Encouraged by computational analysis of [3,3]-sigmatropic rearrangements, we can now rapidly synthesize oxa-heterocycles by treating N-phenoxyacetamides (Ph-ONHAc) with compounds containing an sp-hybridized carbon. The generality of the process is illustrated by the late-stage diversification of natural products, including estrone and an approved drug. A combination of experimental and computational studies revealed that the reactions proceed through a facile Claisen-like [3,3]-sigmatropic rearrangement/annulation process.
- Yan, Dingyuan,Jiang, Heming,Sun, Wenxue,Wei, Wei,Zhao, Jing,Zhang, Xinhao,Wu, Yun-Dong
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p. 1646 - 1653
(2019/09/04)
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- Rhodium(III)-catalysed cascade [3 + 2] annulation of: N -aryloxyacetamides with 3-(hetero)arylpropiolic acids: Synthesis of benzofuran-2(3 H)-ones
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Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).
- Pan, Jin-Long,Liu, Tuan-Qing,Chen, Chao,Li, Quan-Zhe,Jiang, Wei,Ding, Tong-Mei,Yan, Zhi-Qiang,Zhu, Guo-Dong
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p. 8589 - 8600
(2019/10/02)
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- Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides
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A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.
- Wu, Yunxiang,Chen, Zhaoqiang,Yang, Yaxi,Zhu, Weiliang,Zhou, Bing
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- Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization
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A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.
- Pan, Jin-Long,Chen, Chao,Hao, Yu,Liu, Chang,Bai, He-Yuan,Ding, Jun,Zhang, Shu-Yu,Wang, Li-Ren,Xie, Peipei,Xia, Yuanzhi
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p. 7131 - 7136
(2018/12/14)
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- Combination of Cp*RhIII-Catalyzed C?H Activation and a Wagner–Meerwein-Type Rearrangement
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A combination of Cp*RhIII-catalyzed C?H activation and Wagner–Meerwein-type rearrangement was successfully achieved for the first time. Thus, bridged polycyclic molecules that are not readily accessible by other means were accessed under mild c
- Wang, Xiaoming,Lerchen, Andreas,Gensch, Tobias,Knecht, Tobias,Daniliuc, Constantin G.,Glorius, Frank
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p. 1381 - 1384
(2017/01/24)
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- Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
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Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.
- Nimmagadda, Sri Krishna,Mallojjala, Sharath Chandra,Woztas, Lukasz,Wheeler, Steven E.,Antilla, Jon C.
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p. 2454 - 2458
(2017/02/23)
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- 1. 2 - effinity and ring compound derivative as a preparation for treating myeloma drug application
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The invention discloses a 1,2-oxa-cyclic compound derivative and a preparation method thereof. A molecular structural general formula of 1,2-oxa-cyclic compound derivative is (I), wherein in the formula, A is (hetero) aromatic ring or non-aromatic ring; R
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- Rhodium(III)-Catalyzed Annulative Carbooxygenation of 1,1-Disubstituted Alkenes Triggered by C?H Activation
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A Cp*RhIII-catalyzed annulative carbooxygenation of challenging 1,1-disubstituted alkenes triggered by C?H activation of N-aryloxyacetamides has been established, which affords 2,3-dihydrobenzofuran derivatives with a quaternary carbon center i
- Li, Yang,Tang, Yuhai,He, Xin,Shi, Dandan,Wu, Jun,Xu, Silong
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p. 7453 - 7457
(2017/06/06)
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- Cp?Rh(III)/Bicyclic Olefin Cocatalyzed C-H Bond Amidation by Intramolecular Amide Transfer
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A bicyclic olefin was discovered as a cocatalyst in a Cp?Rh(III)-catalyzed C-H bond amidation proceeding by an intramolecular amide transfer in N-phenoxyacetamide derivatives. Combining experimental and theoretical studies, we propose that the olefin promotes a Rh(III) intermediate to undergo oxidative addition into the O-N bond to form a Rh(V) nitrenoid species and subsequently direct the nitrenoid to add to the ortho position. The amide directing group plays a dual role as a cleavable coordinating moiety as well as an essential coupling partner for the C-H amidation. This methodology was successfully applied to the late-stage diversification of natural products and a marketed drug under mild conditions.
- Wang, Xiaoming,Gensch, Tobias,Lerchen, Andreas,Daniliuc, Constantin G.,Glorius, Frank
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p. 6506 - 6512
(2017/05/17)
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- Rhodium(III)-Catalyzed Cascade Redox-Neutral C–H Functionalization and Aromatization: Synthesis of Unsymmetrical ortho-Biphenols
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An efficient rhodium(III)-catalyzed coupling reaction of N-aryloxyacetamides with 6-diazo-2-cyclohexenones through a cascade redox-neutral C–H functionalization and aromatization has been developed. This novel and scalable transformation provides a straightforward way to construct unsymmetrical ortho-biphenols with broad substrate scope under mild and redox-neutral conditions. The synthetic utility of this approach is demonstrated in the late-stage functionalization of bioactive compounds and the synthesis of an optically active ortho-biphenol. (Figure presented.).
- Hu, Zhiyong,Liu, Guixia
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supporting information
p. 1643 - 1648
(2017/05/22)
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- Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials
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Reported herein is the first example of a transition-metal-catalyzed internal oxidative C-H/C-H cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2-(2-hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white-light-emitting materials. As illustrative examples, two bis(triphenylamine)-bearing 2-(2-hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white-light emission, high quantum yield, and thermal stability. Also presented is the first example of the white-light emission, in a single excited-state intramolecular proton transfer system, of 2-(2-hydroxyphenyl)azoles, thus highlighting the charm of C-H activation in the discovery of new organic optoelectronic materials.
- Li, Bijin,Lan, Jingbo,Wu, Di,You, Jingsong
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p. 14008 - 14012
(2016/01/25)
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- Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage
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A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.
- Xie, Ying
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p. 12372 - 12375
(2016/10/22)
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- Unnatural Amino Acid Synthesis Enabled by the Regioselective Cobalt(III)-Catalyzed Intermolecular Carboamination of Alkenes
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Herein, we report an unprecedented regioselective and entirely atom-economic cobalt(III)-catalyzed method for the non-annulative, intermolecular carboamination of alkenes. The methodology enables the direct synthesis of unnatural amino acid derivatives an
- Lerchen, Andreas,Knecht, Tobias,Daniliuc, Constantin G.,Glorius, Frank
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p. 15166 - 15170
(2016/11/25)
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- Rh(iii)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates
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Here we report a new and mild Rh(iii)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates. This reaction provided a straightforward way for installing both an α-quaternary carbon center and a free-OH moiety into the phenyl ring, thus giving access to useful 2-(2-hydroxyphenyl)-2-alkoxymalonates with good substrate/functional group tolerance. This journal is
- Zhou, Jie,Shi, Jingjing,Liu, Xuelei,Jia, Jinlong,Song, Huacan,Xu, H. Eric,Yi, Wei
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p. 5868 - 5871
(2015/03/30)
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- Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
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The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor-acceptor complexes of the oximes and Et3N was proposed as a key step of this process.
- Davies, Jacob,Booth, Samuel G.,Essafi, Stephanie,Dryfe, Robert A. W.,Leonori, Daniele
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supporting information
p. 14017 - 14021
(2016/01/25)
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- Metal-free one-pot synthesis of benzofurans
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Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B. Just add salt! A metal-free, room temperature arylation of ethyl acetohydroxamate, followed by an in situ reaction with ketones under acidic conditions yielded substituted benzo[b]furans in a fast and operationally simple one-pot fashion without using excess reagents (see scheme). Alternatively, the O-arylated products could be isolated, hydrolyzed in situ to aryloxyamines, or transformed to O-arylaldoximes. The efficiency of the methodology was demonstrated by the formal synthesis of several biologically active benzofurans.
- Ghosh, Raju,Stridfeldt, Elin,Olofsson, Berit
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supporting information
p. 8888 - 8892
(2014/07/22)
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- Rhodium(iii)-catalyzed C-H activation/[4+3] annulation of N-phenoxyacetamides and α,β-unsaturated aldehydes: An efficient route to 1,2-oxazepines at room temperature
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An efficient Rh(iii)-catalyzed coupling reaction of N-phenoxyacetamides with α,β-unsaturated aldehydes to give 1,2-oxazepines via C-H activation/[4+3] annulation has been developed. This transformation does not require oxidants and features C-C/C-N bond formation to yield seven-membered oxazepine rings at room temperature. Further derivation of 1,2-oxazepines leads to important chroman derivatives. This journal is
- Duan, Pingping,Lan, Xia,Chen, Ying,Qian, Shao-Song,Li, Jie Jack,Lu, Liang,Lu, Yanbo,Chen, Bo,Hong, Mei,Zhao, Jing
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p. 12135 - 12138
(2014/12/11)
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- Scalable, transition-metal-free direct oxime o-arylation: Rapid access to o-arylhydroxylamines and substituted benzo[b]furans
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O-Aryloximes, generated from readily available and inexpensive oximes through transition-metal-free O-arylation, can either be hydrolyzed to O-arylhydroxylamines or conveniently converted to structurally diverse benzo[b]furans through an environmentally benign, one-pot [3,3]-sigmatropic rearrangement/cyclization sequence. A scalable, transition-metal-free (TM-free) direct O-arylation of ketone oximes with a wide range of diaryliodonium salts has been developed. More than two dozen O-arylated oximes have been prepared in good to excellent yields at ambient temperature and were converted to the corresponding substituted benzo[b]furans through a [3,3]-sigmatropic rearrangement/cyclization sequence. Overall, this operationally simple, environmentally benign, and protecting-group-free approach, including a one-pot variant, allows rapid and convenient synthetic access to substituted benzo[b]furans (see scheme).
- Gao, Hongyin,Xu, Qing-Long,Keene, Craig,Kuerti, Laszlo
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supporting information
p. 8883 - 8887
(2014/07/22)
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- Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity
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Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright
- Liu, Guixia,Shen, Yangyang,Zhou, Zhi,Lu, Xiyan
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p. 6033 - 6037
(2013/07/19)
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- Rhodium(III)-catalyzed C-H olefination for the Synthesis of ortho-alkenyl phenols using an oxidizing directing group
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By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.
- Shen, Yangyang,Liu, Guixia,Zhou, Zhi,Lu, Xiyan
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p. 3366 - 3369
(2013/07/26)
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- AGONISTS OF GPR40
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The present invention relates to compounds that have the ability to modulate the activity of GPR40 and are there-fore useful in the treatment of GPR40 related disorders. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders related to GPR40 activity.
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Page/Page column 175-176
(2012/02/05)
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- Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation
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An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.
- Guru, Murali Mohan,Ali, Md Ashif,Punniyamurthy, Tharmalingam
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p. 5295 - 5308
(2011/08/05)
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- HETEROCYCLIC OXIME COMPOUNDS
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The invention relates to compounds of formula (I) and salts thereof wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).
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Page/Page column 111
(2011/04/13)
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- Copper(II)-catalyzed conversion of bisaryloxime ethers to 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bonds formation
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A copper(II)-catalyzed conversion of bisaryloxime ethers to 2-arylbenzoxazoles has been developed. The reaction involves a cascade C-H functionalization and C-N/C-O bond formation under oxygen atmosphere.(Figure Presented)
- Guru, Murali Mohan,Ali, Md Ashif,Punniyamurthy, Tharmalingam
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body text
p. 1194 - 1197
(2011/04/26)
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- Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group
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A series of new structural benzoylphenylureas (BPUs) containing oxime ether and oxime ester group were designed and synthesized. The larvicidal activities against Oriental armyworm and mosquito of these benzoylphenylureas were evaluated and the result of bioassay displayed specific structure-activity relationship (SAR). Most of the compounds exhibited excellent larvicidal activities against Oriental armyworm and mosquito. Interestingly, some compounds showed different structure-activity relationship towards diamondback moth, beet armyworm, and corn borer although three tested insects all belong to the same insect order.
- Sun, Ranfeng,Li, Yongqiang,Lue, Maoyun,Xiong, Lixia,Wang, Qingmin
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scheme or table
p. 4693 - 4699
(2010/10/02)
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- Fluorous tagged N-hydroxy phthalimide for the parallel synthesis of O-aryloxyamines
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The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acid
- Gaucher-Wieczorek, Florence S.,Maillard, Ludovic T.,Badet, Bernard,Durand, Philippe
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scheme or table
p. 655 - 658
(2010/10/21)
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- Direct preparation of benzofurans from O-arylhydroxylamines
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Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran derivative via a proposed one-pot condensation-rearrangement- cyclisation reaction sequence in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Contiero, Fanny,Jones, Kevin M.,Matts, Edward A.,Porzelle, Achim,Tomkinson, Nicholas C.O.
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scheme or table
p. 3003 - 3006
(2010/03/03)
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- 3,6-Bicyclolides
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The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.
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Page/Page column 52
(2008/06/13)
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- Inhibitors of transthyretin amyloid fibril formation
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Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.
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Page/Page column 8; sheet 6
(2008/06/13)
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- Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation
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Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.
- Johnson, Steven M.,Petrassi, H. Michael,Palaninathan, Satheesh K.,Mohamedmohaideen, Nilofar N.,Purkey, Hans E.,Nichols, Christopher,Chiang, Kyle P.,Walkup, Traci,Sacchettini, James C.,Sharpless, K. Barry,Kelly, Jeffery W.
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p. 1576 - 1587
(2007/10/03)
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- The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.
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[figure: see text] A novel route to aryloxyamines via the copper-mediated cross-coupling of N-hydroxyphthalimide and phenylboronic acids is reported. The reaction is mediated by selected copper(I) and (II) salts in the presence of pyridine and is tolerant of several functional groups on the phenylboronic acid. The phthallmide group is removed using hydrazine to afford the corresponding aryloxyamine.
- Petrassi,Sharpless,Kelly
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p. 139 - 142
(2007/10/03)
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- Nodulisporic acid derivatives
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The present invention relates to novel nodulosporic acid derivatives, which are acaricidal, antiparasitic, insecticidal and anthelmintic agents.
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- Imine exchange in O-aryl and O-alkyl oximes as a base reaction for aqueous 'dynamic' combinatorial libraries. A kinetic and thermodynamic study
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Kinetics and mechanisms of the imine exchange reactions of O-alkyl and O-aryl oximes with O-alkyl-and O-aryloxyamines, respectively, were studied by 1H NMR spectroscopy in aqueous solutions. The reaction between benzaldehyde O-methyloxime and O-ethylhydroxylamine at 60 °C is first order in both oxime and the alkoxylamine (the second-order rate constant k2 = 0.86 ± 0.081 mol-1 min-1 at pD 2.9). the reaction being subject to acidic catalysis. A similar imine transfer was studied in the reaction of 1,3-diaminooxyprog with bifunctional oximes. Testing of various additives as potential catalysts for the reaction revealed imidazole as a moderately effective catalyst. The exchange in O-aryl oximes was studied in the interaction between 3-pyridinealdehyde O-pnenyloxime and O-(p-nitrophenyl)hydroxylamine. The reaction is first order in the oxime, but its is independent on the aryloxyamine concentration and pD. The proposed mechanism involves a rate-limiting hydration of the oxime molecule. Mechanisms of the exchange reactions are discussed in relation to their possible use to generate diverse pools of compounds for the recently proposed 'dynamic' combinatorial chemistry approach Copyright
- Polyakov, Vladimir A.,Nelen, Marina I.,Nazarpack-Kandlousy, Noureddin,Ryabov, Alexander D.,Eliseev, Alexey V.
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p. 357 - 363
(2007/10/03)
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