cas 83515-06-4, 1H-INDOLE, 5-BROMO-2-PHENYL-

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Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
supporting information
p. 9246 - 9250
(2021/12/06)

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
Chen, Shaomin,Gu, Yanlong,Li, Minghao
supporting information
p. 10431 - 10434
(2021/10/12)

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
supporting information
p. 9610 - 9616
(2021/12/09)

Modular counter-Fischer?indole synthesis through radical-enolate coupling
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information
p. 1096 - 1102
(2021/01/26)

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
supporting information
p. 10242 - 10245
(2021/10/12)

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
supporting information
p. 3294 - 3299
(2020/01/21)

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
p. 7433 - 7445
(2020/06/27)

Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones
A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.
Dong, Chun-Lin,Ding, Xuan,Huang, Lan-Qian,He, Yan-Hong,Guan, Zhi
supporting information
p. 1076 - 1080
(2020/02/15)

Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones
A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.
Chen, Yu-Jue,Chen, Yuan,Ding, Xuan,Guan, Zhi,He, Yan-Hong,Lu, Fo-Yun
supporting information
p. 623 - 626
(2020/01/28)

A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder
An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.
Ni, Penghui,Tan, Jing,Zhao, Wenqi,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
supporting information
p. 3518 - 3522
(2019/05/24)

Metal-Free Double Csp2-H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes
A metal-free strategy for the synthesis of benzocarbazoles from 2-arylindoles and aryl ketones is developed. Various 2-aryl-3-vinyl-indoles were generated in situ through dehydrative condensation of aryl ketones and indoles. These key intermediates could be selectively converted into the corresponding benzo[a]carbazoles via a direct cyclization process between two Csp2-H bonds. Furthermore, terminal alkynes also could be used as the versatile C2 source to afford the corresponding products in good yields.
Ni, Penghui,Tan, Jing,Zhao, Wenqi,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
supporting information
p. 3687 - 3691
(2019/05/24)

Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
supporting information
p. 3527 - 3530
(2018/06/26)

Method for directly synthesizing indole by using nitrile
The invention discloses a method for directly synthesizing indole by using nitrile. The method is characterized in that a 2-iodotoluene derivative is served as a substrate, anhydrous copper sulfate, potassium tert-butoxide, a cyanophenyl derivative and the 2-iodophene derivative are mixed according to the molar ratio of (0.02-0.1): (2-4): (5-20):1, reaction is carried out for 4-48 hours at 60-105DEG C in a solvent, petroleum ether/dichloromethane/ethyl acetate are mixed according to the volume ratio of (20-5):10:1 so as to be served as an eluent, and separation is carried out by using a silica gel column so as to obtain a target product. The method has the advantages that the operation is simple, the conditions are mild, the yield is high, and the method is a green and novel synthetic method.
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Paragraph 0015-0017

(2018/12/13)

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.
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Paragraph 0439-0443

(2018/08/30)

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1
In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.
Prior, Allan M.,Yu, Xufen,Park, Eun-Jung,Kondratyuk, Tamara P.,Lin, Yan,Pezzuto, John M.,Sun, Dianqing
p. 5393 - 5399
(2017/11/20)

Method for synthesizing aryl-substituted indole compound serving as drug intermediate
The invention relates to a method for synthesizing an indole compound which is shown as the following formula (III) and is capable of serving as a drug intermediate. The method comprises the steps of in the atmosphere of neutralizing an inert gas by using a solvent and in the presence of a catalyst, a nitrogen-containing ligand and an acid accelerator, reacting a compound shown as the following formula (I) with a compound shown as the following formula (II), and carrying out aftertreatment after completing the reaction, thereby obtaining the compound shown as the following formula (III), wherein the R1 is selected from H or halogen; the R2 is selected from H, C1-C6 alkyl, C1-C6 alkoxy or halogen; or the R2 is together with R2-substituted phenyl to form naphthyl. The method has the advantages that through the comprehensive selection and the synergy of appropriate substrate, catalyst, nitrogen-containing ligand, acid accelerator, solvent and the like, the range of the substrate is expanded and the aryl-substituted indole compound with good yield can be obtained, so that the method has good application prospect and research value in the field of organic chemical synthesis and a novel method for synthesizing the compounds is provided.
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Paragraph 0070-0073

(2017/09/01)

Synthetic method of medical intermediate 2-arylindole compound
The invention relates to a synthetic method of a 2-arylindole compound shown as a formula (III) and capable of being used as a medical intermediate. The method comprises the following steps that in a solvent and inert gas atmosphere, a compound shown as a formula (I) and a compound shown as a formula (II) take a reaction under the existence of the solvent, a nitrogen-containing ligand and an acidic accelerator; after the reaction is finished, aftertreatment is performed, so that a compound shown as a formula (III) is obtained; the formulas are shown in the description, wherein R1 is selected from H or halogen; R2 is selected from H, C1-C6 alkyls, C1-C6 alkoxys or halogen, or the R2 and the substituted phenyl form a naphthyl. The method has the advantages that through the comprehensive selection and cooperation of a proper substrate, the catalyst, the nitrogen-containing ligand, the acidic accelerator, the solvent and the like, so that the 2-arylindole compound with good yield can be obtained; good application prospects and research values are realized in the field of organic chemical synthesis; a bran-new method is provided for the compound synthesis.
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Paragraph 0070; 0071; 0072; 0073

(2017/08/31)

Palladium-catalyzed tandem addition/cyclization in aqueous medium: Synthesis of 2-arylindoles
An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.
Yu, Shuling,Hu, Kun,Gong, Julin,Qi, Linjun,Zhu, Jianghe,Zhang, Yetong,Cheng, Tianxing,Chen, Jiuxi
p. 4300 - 4307
(2017/07/10)

The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.
Yu, Shuling,Qi, Linjun,Hu, Kun,Gong, Julin,Cheng, Tianxing,Wang, Qingzong,Chen, Jiuxi,Wu, Huayue
p. 3631 - 3638
(2017/04/11)

Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation
A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.
Gao, Yadong,Zhu, Wangying,Yin, Long,Dong, Bo,Fu, Jingjing,Ye, Zhiwen,Xue, Fengtian,Jiang, Chao
supporting information
p. 2213 - 2216
(2017/05/16)

Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles
An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
Liu, Congrong,Yang, Fulai
supporting information
p. 1213 - 1217
(2016/12/28)

Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform
The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.
Huang, Yuan-Biao,Shen, Min,Wang, Xusheng,Huang, Ping,Chen, Ruiping,Lin, Zu-Jin,Cao, Rong
p. 1 - 7
(2015/11/24)

Method for synthesizing indole derivative
The invention relates to a method for synthesizing an indole derivative shown in the formula (III) (please see the specification). The method includes the steps that in a solvent and inertia gas atmosphere, when a catalyst, a nitrogen-containing ligand, an acid accelerator and KF exist, a compound in the formula (I) (please see the specification) and a compound in the formula (II) (please see the specification) are reacted, aftertreatment is carried out after the reaction is completed, and therefore the compound in the formula (III) is obtained, wherein R1 is selected from H or halogen, and R2 is selected from H, C1-C6 alkyl, C1-C6 alkoxy or halogen. According to the method, as a proper substrate, the proper catalyst, the proper nitrogen-containing ligand, the proper acid accelerator, the proper KF, the proper solvent and the like are comprehensively selected and cooperated, the range of the substrate is expanded accordingly, the indole derivative can be obtained with the good yield, the method has good application prospects and research value in the field of organic chemistry synthesis, and a brand new method is provided for synthesis of the compound.
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(2016/10/10)

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
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Paragraph 0154-0156

(2016/10/07)

Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides
A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.
Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei,Yang, Fu-Lai
p. 2824 - 2827
(2016/03/12)

New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer
We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.
La Regina, Giuseppe,Bai, Ruoli,Coluccia, Antonio,Famiglini, Valeria,Pelliccia, Sveva,Passacantilli, Sara,Mazzoccoli, Carmela,Ruggieri, Vitalba,Verrico, Annalisa,Miele, Andrea,Monti, Ludovica,Nalli, Marianna,Alfonsi, Romina,Di Marcotullio, Lucia,Gulino, Alberto,Ricci, Biancamaria,Soriani, Alessandra,Santoni, Angela,Caraglia, Michele,Porto, Stefania,Da Pozzo, Eleonora,Martini, Claudia,Brancale, Andrea,Marinelli, Luciana,Novellino, Ettore,Vultaggio, Stefania,Varasi, Mario,Mercurio, Ciro,Bigogno, Chiara,Dondio, Giulio,Hamel, Ernest,Lavia, Patrizia,Silvestri, Romano
p. 5789 - 5807
(2015/08/24)

Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C-H Functionalization Cascade
A palladium-catalyzed expeditious synthesis of dibenzofused carbazoles from readily available 2-arylindoles and diaryliodonium salts is reported. Interestingly, after the electrophilic C3 palladation of indole, an unexpected "through-space" 1,4-palladium migration to the 2-aryl moiety, by remote C-H bond activation followed by C-H arylation with diaryliodonium salt, and an unprecedented 1,2-aryl shift take place. Finally, an intramolecular cross-dehydrogenative coupling (CDC) at the C2 position affords dibenzo[a,c]carbazoles in high yields. Remarkably, the present migratory annulation occurs through three C-H bond activation one C-C bond cleavage, and the simultaneous construction of three new C-C bonds in a single operation.
Bhunia, Samir Kumar,Polley, Arghya,Natarajan, Ramalingam,Jana, Ranjan
supporting information
p. 16786 - 16791
(2015/11/16)

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.
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Paragraph 0373-0377

(2016/10/07)

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.
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Paragraph 0099; 0100

(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
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Paragraph 0197; 0198; 0199

(2016/10/08)

This is a novel compound and an organic electroluminescence element including
The present invention relates to a novel compound and an organic electroluminescence device including the same, and the compound according to the present invention may be used in an organic material layer, preferably a light-emitting layer of an organic electroluminescence device, thereby enhancing the light-emitting efficiency, driving voltage, lifespan, and the like of the organic electroluminescence device.
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Paragraph 0101; 0102

(2016/10/08)

Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO
The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is
Hudson,Bizier,Esdale,Katz
p. 2273 - 2284
(2015/03/04)

Multi-site cyclization via initial C-H activation using a rhodium(III) catalyst: Rapid assembly of frameworks containing indoles and indolines
Tandem multi-site cyclization triggered by Rh(III)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.
Huang, Ji-Rong,Qin, Liu,Zhu, Yu-Qin,Song, Qiang,Dong, Lin
supporting information
p. 2844 - 2847
(2015/03/05)

Discovery of indole-based tetraarylimidazoles as potent inhibitors of urease with low antilipoxygenase activity
A series of tetraarylimidazoles (5A-5O) were prepared by one pot four component condensation reactions of 2-arylindole-3-carbaldehydes, substituted anilines, benzil and ammonium acetate in acetic acid. The synthesized compounds exhibited potent antiurease
Naureen, Sadia,Chaudhry, Faryal,Asif, Nadia,Munawar, Munawar Ali,Ashraf, Muhammad,Nasim, Faizul Hassan,Arshad, Humera,Khan, Misbahul Ain
p. 464 - 470
(2015/09/01)

A Mild Approach for the Synthesis of Indoles from N -(2-Iodo-aryl)formAamides and Phenylacetylene by a Copper(I)- and Palladium-Catalyzed Cascade Process
An efficient one-pot copper(I)- and palladium-catalyzed synthesis of indoles from N-(2-iodo-aryl)formamides and phenylAacetylene is described. The cascade reaction comprises a Sonogashira cross-coupling, an intramolecular C-N bond formation, and hydrolysi
Ahmed, Atiur,Ghosh, Munmun,Dhara, Shubhendu,Ray, Jayanta K.
p. 2455 - 2458
(2015/07/27)

Synthesis of 2-Substituted Indoles through Visible Light-Induced Photocatalytic Cyclizations of Styryl Azides
A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.
Xia, Xu-Dong,Xuan, Jun,Wang, Qiang,Lu, Liang-Qiu,Chen, Jia-Rong,Xiao, Wen-Jing
p. 2807 - 2812
(2016/02/18)

Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
2-Bromo(chloro)indoles were readily and efficiently prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions. This journal is the Partner Organisations 2014.
Wang, Min,Li, Pinhua,Chen, Wei,Wang, Lei
p. 26918 - 26923
(2014/07/21)

Palladium-catalyzed synthesis of 3-acylated indoles involving oxidative cross-coupling of indoles with α-amino carbonyl compounds
A new and selective C-N bond oxidative cleavage method to 3-acylated indoles by Pd-catalyzed oxidative cross coupling of indoles with α-amino carbonyl compounds has been developed; moreover, one-pot synthesis of 3-acylated indoles from 2-ethynylanilines and α-amino carbonyl compounds has also been established. Importantly, the products 3-acylated indoles can be used to construct polyheterocyclic compound, which can be employed as efficient probes for Hg2+ and Fe3+.
Tang, Ri-Yuan,Guo, Xiao-Kang,Xiang, Jian-Nan,Li, Jin-Heng
p. 11163 - 11171
(2013/12/04)

SUBSTITUTED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.
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(2013/03/26)

Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
supporting information
p. 8196 - 8198
(2013/09/12)

Microwave-accelerated Pd-catalyzed desulfitative direct C2-arylation of free (NH)-indoles with arylsulfinic acids
The rapid and efficient direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a microwave-accelerated palladium-catalyzed desulfitation reaction. By using PdCl2 as a catalyst, silver acetate as an oxidant, and H2SO4 as an additive, arylsulfinic acids with both electron-donating and electron-withdrawing groups underwent desulfitative coupling with an array of free (NH)-indoles, thereby selectively providing C2-arylindoles in good yields. From C2 shining sea: The direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a Pd-catalyzed desulfitation reaction. In the presence of an oxidant and an additive, 2-arylindoles were selectively afforded in good yields. Copyright
Miao, Tao,Li, Pinhua,Wang, Guan-Wu,Wang, Lei
p. 3185 - 3190
(2014/01/06)

PROCESSES FOR PREPARING INDOLES
Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.
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(2013/07/05)

Synthesis of 2-arylindole derivatives and evaluation as nitric oxide synthase and NFκB inhibitors
Development of small molecule drug-like inhibitors blocking both nitric oxide synthase and NFκB could offer a synergistic therapeutic approach in the prevention and treatment of inflammation and cancer. During the course of evaluating the biological potential of a commercial compound library, 2-phenylindole (1) displayed inhibitory activity against nitrite production and NFκB with IC50 values of 38.1 ± 1.8 and 25.4 ± 2.1 μM, respectively. Based on this lead, synthesis and systematic optimization have been undertaken in an effort to find novel and more potent nitric oxide synthase and NFκB inhibitors with antiinflammatory and cancer preventive potential. First, chemical derivatizations of 1 and 2-phenylindole-3-carboxaldehyde (4) were performed to generate a panel of N-alkylated indoles and 3-oxime derivatives 2-7. Second, a series of diversified 2-arylindole derivatives (10) were synthesized from an array of substituted 2-iodoanilines (8) and terminal alkynes (9) by applying a one-pot palladium catalyzed Sonogashira-type alkynylation and base-assisted cycloaddition. Subsequent biological evaluations revealed 3-carboxaldehyde oxime and cyano substituted 2-phenylindoles 5 and 7 exhibited the strongest nitrite inhibitory activities (IC50 = 4.4 ± 0.5 and 4.8 ± 0.4 μM, respectively); as well as NFκB inhibition (IC50 = 6.9 ± 0.8 and 8.5 ± 2.0 μM, respectively). In addition, the 6′-MeO-naphthalen-2′-yl indole derivative 10at displayed excellent inhibitory activity against NFκB with an IC50 value of 0.6 ± 0.2 μM.
Yu, Xufen,Park, Eun-Jung,Kondratyuk, Tamara P.,Pezzuto, John M.,Sun, Dianqing
p. 8835 - 8847
(2013/01/15)

AROMATIC HETEROCYCLIC DERIVATIVE HAVING TRPV4-INHIBITING ACTIVITY
A compound having TRPV4 inhibitory activity or a pharmaceutically acceptable salt thereof is provided. The present invention is related to a compound represented by the formula (I). wherein R1a is substituted or unsubstituted alkyl or the like;
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(2012/11/07)

Copper catalysed domino decarboxylative cross coupling-cyclisation reactions: Synthesis of 2-arylindoles
The efficient synthesis of 2-arylindoles and 6H-isoindolo[2,1-a]indol-6-one through copper catalysed domino sp-sp2 decarboxylative cross-coupling and subsequent cyclisation reactions of arylpropiolic acids with 2-iodotrifluoroacetanilide has been described. This methodology also demonstrates that indolo[1,2-c]quinazolin-6(5H)-one can be obtained with the elimination of trifluoromethyl anion.
Ponpandian, Thanasekaran,Muthusubramanian, Shanmugam
p. 4248 - 4252
(2012/08/28)

"on water" direct and site-selective Pd-catalysed C-H arylation of (NH)-indoles
This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [Pd(OAc)2/dppm] that works "on water" giving site-selective C-H arylation of (NH)-indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the "extra-catalytic" base/halide partners. These innovative methodologies allow a high-yielding access to both C2 and C3-arylindoles, as well as 2,3-diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties. Copyright
Joucla, Lionel,Batail, Nelly,Djakovitch, Laurent
supporting information; experimental part
p. 2929 - 2936
(2011/02/22)

Methods and systems for preparing fused heterocyclic compounds using copper(I) catalysts
A copper(I)-catalyzed procedure for the synthesis of benzo[b]heterocycles. This protocol can be used to synthesize a variety of 2-arylbenzo[b]furans and indoles in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives and is palladium-free.
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(2009/01/24)

Molecular engineering of organic sensitizers containing indole moiety for dye-sensitized solar cells
Three organic dyes, JK-77, JK-78, and JK-79 containing indole unit are designed and synthesized. Nanocrystalline TiO2 dye-sensitized solar cells were fabricated using these dyes. Under standard global AM 1.5 solar condition, the JK-79 sensitize
Kim, Duckhyun,Kang, Moon-Sung,Song, Kihyung,Kang, Sang Ook,Ko, Jaejung
p. 10417 - 10424
(2008/12/23)

Room temperature palladium-catalyzed 2-arylation of indoles
This communication describes the rational development of a PdII-catalyzed method for the direct 2-arylation of indoles using [Ar-IIII-Ar]BF4. These reactions proceed under remarkably mild conditions (often at room temperature and in the presence of ambient air and moisture), and these features are believed to be the result of a PdII/IV mechanism operating in these systems. These transformations can be used to prepare functionally diverse 2-arylated indoles and pyrroles, and their potential utility has been expanded by the development of an in situ procedure for generating the iodine(III) arylating reagents. Copyright
Deprez, Nicholas R.,Kalyani, Dipannita,Krause, Andrew,Sanford, Melanie S.
p. 4972 - 4973
(2007/10/03)

Copper(I)-catalyzed coupling of terminal acetylenes with aryl or vinyl halides
Synthetic protocols using copper(I) catalysts for the formation of diaryl acetylenes, 1,3-enynes, benzofurans and indoles are described. Georg Thieme Verlag Stuttgart.
Saejueng, Pranorm,Bates, Craig G.,Venkataraman
p. 1706 - 1712
(2007/10/03)