- Suzuki–Miyaura Cross-Coupling Reactions of Tetrahydroxanthones and 4-Chromanone Lactones to Heteromeric Biaryls
-
We are reporting on a Suzuki–Miyaura cross-coupling study of a tetrahydroxanthone model system with different boronic acids, pinacolboranes, and halides to afford heteromeric biaryls. We transferred these reaction conditions to the Suzuki–Miyaura cross-coupling reactions of 4-chromanone lactones. We thereby obtained complex building blocks offering a convenient starting point for further transformations towards various natural products with the tetrahydroxanthone structural motif. (Figure presented.).
- Geiger, Larissa,Nieger, Martin,Br?se, Stefan
-
-
Read Online
- Preparation method of indole type or aniline type borate
-
The invention discloses a preparation method of indole type or aniline type borate, which comprises the following step: reacting an indole type raw material or aniline type raw material with boron trihalide in an organic solvent under the protection of in
- -
-
Paragraph 0045-0047
(2020/06/17)
-
- Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex
-
Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.
- Zhao, Jia-Hui,Zhou, Zhao-Zhao,Zhang, Yue,Su, Xuan,Chen, Xi-Meng,Liang, Yong-Min
-
supporting information
p. 4390 - 4394
(2020/10/20)
-
- Metal-free directed sp 2-C–H borylation
-
Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can
- Lv, Jiahang,Chen, Xiangyang,Xue, Xiao-Song,Zhao, Binlin,Liang, Yong,Wang, Minyan,Jin, Liqun,Yuan, Yu,Han, Ying,Zhao, Yue,Lu, Yi,Zhao, Jing,Sun, Wei-Yin,Houk, Kendall. N.,Shi, Zhuangzhi
-
p. 336 - 340
(2019/11/14)
-
- Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3
-
Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.
- Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.
-
p. 15381 - 15385
(2019/10/22)
-
- ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
-
The present invention relates to an indole-based compound with excellent hole injection and hole transport ability; and to an organic electroluminescent device which includes the compound in one or more layers and thus has increased light emitting efficiency, needs lower driving voltages, and has an extended life span. According to the present invention, the electroluminescent device includes: (i) a positive electrode; (ii) a negative electrode; and (iii) one or more organic layers interposed between the positive electrode and the negative electrode.
- -
-
Paragraph 0186; 0188; 0189; 0224-0227
(2018/08/30)
-
- 2-ARYLAMINO PYRIDINE, PYRIDINE OR TRIAZINE DERIVATIVE, PREPARATION METHOD AND USE THEREOF
-
The present disclosure relates to 2-arylamino pyridine, pyrimidine, or triazine derivatives, and the preparation method and use thereof. The 2-arylamino pyridine, pyrimidine, or triazine derivatives may act on certain mutated forms of epidermal growth fac
- -
-
Paragraph 0332; 0333
(2018/07/29)
-
- Total Syntheses of the Amaryllidaceae Alkaloids Zephycandidine III and Lycosinine A and Their Evaluation as Inhibitors of Acetylcholinesterase
-
The title alkaloids, 1 and 2, have been prepared using cross-coupling chemistries and together with various analogues they have been evaluated for their capacity to inhibit acetylcholinesterase. Contrary to an earlier report, it was found that biaryl 1 is not a significant inhibitor of this enzyme, and neither are any of its congeners, including alkaloid 2.
- Xu, Xingjun,Kim, Hye-Sun,Chen, Wei-Min,Ma, Xiang,Correy, Galen J.,Banwell, Martin G.,Jackson, Colin J.,Willis, Anthony C.,Carr, Paul D.
-
p. 4044 - 4053
(2017/07/28)
-
- Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
-
Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.
- Taylor, Nicholas J.,Emer, Enrico,Preshlock, Sean,Schedler, Michael,Tredwell, Matthew,Verhoog, Stefan,Mercier, Joel,Genicot, Christophe,Gouverneur, Véronique
-
supporting information
p. 8267 - 8276
(2017/06/27)
-
- Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles
-
Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.
- Shen, Fangyi,Tyagarajan, Sriram,Perera, Damith,Krska, Shane W.,Maligres, Peter E.,Smith, Milton R.,Maleczka, Robert E.
-
p. 1554 - 1557
(2016/05/02)
-
- ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT ELEMENT USING THE SAME
-
PROBLEM TO BE SOLVED: To provide an indole-based compound excellent in hole injection, hole transport capability and light-emitting capability and to provide an organic electroluminescent element that includes the compound in an organic layer and is excellent in characteristics such as luminous efficiency, drive voltage, life and the like. SOLUTION: The indole-based compound is represented by the formula as given below and the organic electroluminescent element includes the compound in one or more organic layers. [R1 and R2 are each independently H, D, alkyl or the like; Y3 to Y8 are CR4; R4s are each independently H, D, alkyl, aryl or the like; Z1 to Z6 are each independently N or AR6; AR6A and B are each independently alkylcycloalkyl, aryl, heteroaryl or the like; p and q are each independently an integer of 0 to 3; r and s are each independently an integer of 0 to 5; and r+s≥1] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
- -
-
Paragraph 0039; 0040; 0058; 0059
(2016/10/07)
-
- Preparation of No-Carrier-Added 6-[18F]Fluoro-l-tryptophan via Cu-Mediated Radiofluorination
-
18F-Labeled aromatic amino acids exhibit great potential for diagnostic applications using positron emission tomography. However, the introduction of18F into aromatic compounds remains challenging, and novel fluorination methods facilitating easy access to18F-labeled arenes are highly sought after. In recent years, novel metal-mediated fluorination methods have been reported and transferred into radiochemistry. Based on Cu-mediated radiofluorination, a two-step synthesis of no-carrier-added (n.c.a.) 6-[18F]fluoro-l-tryptophan was developed. 6-[18F]Fluoro-l-tryptophan was synthesized with an overall radochemical yield of 16 ± 4% within 110 min and a specific activity of 280 GBq μmol–1. The radiochemical purity was more than 99 %. The developed method allowed access to radiofluorinated tryptophan derivatives in high radiochemical yields and opens new ways to provide radiofluorinated amino acids. Furthermore, the reaction conditions were optimized to facilitate automation.
- Sch?fer, Dominique,Wei?, Philipp,Ermert, Johannes,Castillo Meleán, Johnny,Zarrad, Fadi,Neumaier, Bernd
-
p. 4621 - 4628
(2016/09/28)
-
- NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME
-
The present disclosure relates to a novel compound having excellent hole injection capabilities and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescent device which includes the compound in one or more organic material layers thereof so as to improve characteristics such as light-emitting efficiency, driving voltage, and a service life.
- -
-
-
- ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
-
The present invention refers to a fullerene derivative is denoted by chemical formula 1 a and is provided to improve quality of an organic electroluminescent including, a fullerene derivative is denoted by chemical formula 1 a at least one organic layer, preferably hole injection layer, hole transport layer and/or a light emitting layer by the inclusion of, said compound hole injection ability, hole transport ability, since light emitting ability selected from the group consisting of triazole, the P-type semiconductor layer, , driving voltage, longevity, etc. can be are formed: [Formula 1] (Said formula 1 in, L, X 1, X 2, Cy1, Cy2 each that are defined in the detailed description as).
- -
-
Paragraph 0171; 0290-0293
(2016/10/08)
-
- ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
-
The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emission, and other properties, and to an organic electroluminescent device the luminous efficiency, driving voltage, service
- -
-
Page/Page column
(2015/08/04)
-
- NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE INCLUDING THESAME
-
The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescence device which includes the indole-based compound in one or more organic material layers thereof so as to improve characteristics such as light-emitting efficiency, driving voltage, and lifespan.
- -
-
-
- ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
-
The present invention refers to hole injection and transporting ability, light emitting ability selected from the group consisting of triazole new organic compound and said at least one compound organic luminous efficiency by the inclusion of layer, driving voltage, longevity, etc. are formed on the relates to organic electroluminescence device.
- -
-
Paragraph 0174; 0175; 0229-0232
(2016/10/07)
-
- ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME
-
The present invention relates to organic compounds and an organic electroluminescent device comprising the same. According to the present invention, the organic compounds can improve light emitting efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device by being used in an organic layer, desirably a light emitting layer of the organic electroluminescent device. The compounds are represented by chemical formula 1.COPYRIGHT KIPO 2015
- -
-
Paragraph 0095; 0096; 0097; 0154-0156
(2016/10/08)
-
- Organic light emitting compd. and organic electroluminescence element using the same
-
The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emission, and other properties, and to an organic electroluminescent device the luminous efficiency, driving voltage, service life, and other characteristics of which are improved due to containing the compound in one or more organic material layers.
- -
-
Paragraph 0045-0046; 0079
(2016/10/24)
-
- This is a novel compound and an organic electroluminescence element including
-
The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescence device which includes the indole-based compound in one or more organic material layers thereof so as to improve characteristics such as light-emitting efficiency, driving voltage, and lifespan.
- -
-
Paragraph 0047; 0065
(2016/10/07)
-
- Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles
-
Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright
- Robbins, Daniel W.,Boebel, Timothy A.,Hartwig, John F.
-
supporting information; experimental part
p. 4068 - 4069
(2010/05/01)
-
- Synthesis of some new biheterocycles by a one-pot Suzuki-Miyaura coupling reaction
-
Halogenated indoles, benzofurans and flavones were subjected to a one-pot Suzuki-Miyaura coupling reaction to generate a series of new biheterocycles. The methodology may be readily adapted to the synthesis of a wide variety of substituted biheterocycles.
- Deodhar, Mandar,Black, David Stc.,Shiu-Hin Chan, Daniel,Kumar, Naresh
-
experimental part
p. 1267 - 1274
(2010/10/05)
-
- INTRACELLULAR RECEPTOR MODULATOR COMPOUNDS AND METHODS
-
This invention relates to compounds of Formula I, II or III with the definitions of R1-R10 according to claim 1 that bind to intracellular receptors and/or modulate activity of intracellular receptors, and to methods for making and using such compounds.
- -
-
Page/Page column 126
(2010/10/20)
-
- Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation
-
Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary. Copyright
- Paul, Sulagna,Chotana, Ghayoor A.,Holmes, Daniel,Reichle, Rebecca C.,Maleczka Jr., Robert E.,Smith III, Milton R.
-
p. 15552 - 15553
(2007/10/03)
-
- Comparative study of the Kumada, Negishi, Stille, and Suzuki - Miyaura reactions in the synthesis of the indole alkaloids hippadine and pratosine
-
The total synthesis of hippadine by a tandem metalation/cross-coupling/ lactamization strategy was investigated starting from either 7-bromoindole or a 6-halogenated methyl piperonate. The Kumada and Negishi cross-coupling reactions failed to provide any of the desired product. However, the Stille and Suzuki reactions furnished hippadine in low yields starting from the electron-deficient methyl 6-iodo- and 6-bromopiperonate, respectively. Starting from the metalated indole, only the Suzuki reaction occurred, affording hippadine in 67-74% and pratosine in 62% isolated yield.
- Mentzel, Uffe V.,Tanner, David,Tonder, Janne E.
-
p. 5807 - 5810
(2007/10/03)
-
- MINERALOCORTICOID RECEPTOR MODULATOR COMPOUNDS AND METHODS
-
This invention relates to compounds that bind to mineralocorticoid receptors and/or modulate activity of mineralocorticoid receptors, and to methods for making and using such compounds.
- -
-
Page/Page column 83; 84
(2008/06/13)
-
- Microwave enhanced formation of electron rich arylboronates
-
Microwave assisted synthesis of eight electron rich aryl boronates (2a-c, 4, 6a-d) via palladium catalyzed reactions of the corresponding aryl bromides with bis(pinacolato)diboron are described. Compared to conventional heating conditions, dramatic rate e
- Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim
-
p. 1204 - 1206
(2007/10/03)
-