cas 19402-87-0, 9-Benzylcarbazole | Articles data

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Accelerative effects of carbazole-type alkaloids from Murraya koenigii on neurite outgrowth and their derivative’s in vivo study for spatial memory
Murraya koenigii is a medicinal plant that contains several carbazole-type alkaloids as its characteristic constituents. Blood–brain barrier permeable constituents of M. koenigii accelerated neurite outgrowth in PC-12 cells. Nine compounds were isolated f
Yano, Mamiko,Nakashima, Souichi,Kasa, Shiori,Nakamura, Seikou,Nishimura, Kaneyasu,Oda, Yoshimi,Takata, Kazuyuki,Matsuda, Hisashi
p. 448 - 455
(2020)
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New carbazole alkaloids from Murraya euchrestifolia
Two new monomeric and one dimeric carbazole alkaloids were isolated from root bark of Murraya euchrestifolia HAYATA collected in Taiwan. Their structures were elucidated by spectrometric and synthetic studies. The structures of the monomeric carbazoles were assigned as 3-formyl-7-hydroxy-9H-carbazole (1) and N-methoxy-3-hydroxymethyl 9H-carbazole (2). The dimeric carbazole, named chrestifoline-D (9), was found to be identical with the oxidation product of bismurrayafoline-A (10).
Ito,Okahana,Wu,Wang,Lai,Kuoh,Furukawa
p. 230 - 232
(1992)
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Thermally activated delayed fluorescence in 1,3,4-oxadiazoles with π-extended donors
Here, we describe the synthesis of five 1,3,4-oxadiazole-based donor-acceptor materials, using dendritic carbazole-based donors 9′H-9,3′:6′9″-tercarbazole (terCBz) and N3,N3,N6,N6-tetra-p-tolyl-9H-carbazole-3,6-diamine (TTAC). Due to the strongly donating and highly twisted nature of the TTAC donor as well as the spatially separated hole-particle wavefunctions, three of the five compounds exhibited thermally activated delayed fluorescence (TADF) in spite of a relatively large ΔEST measured through phosphorimetry (0.33-0.37 eV). These materials demonstrated photoluminescence quantum yields as high as 0.89 in toluene, with emission maxima ranging from 474 to 495 nm in the solid state. Additionally, two materials containing only terCBZ donor(s) exhibited deep blue fluorescence, with Commission Internationale de l'éclairage coordinates of (0.16, 0.05); the weaker nature of the terCBz donor results in a prohibitively large ΔEST (0.68-0.77 eV). A gap-tuned range-separated hybrid functional (ωB97XD*) was used to rigorously calculate triplet energies, while a systematic analysis of electronic structures and photophysical properties provided further insight into the properties of these materials. These findings ultimately contribute a synthetically facile approach toward highly emissive TADF emitters using a 1,3,4-oxadiazole motif.
Mayder, Don M.,Tonge, Christopher M.,Hudson, Zachary M.
p. 11094 - 11103
(2020)
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THE APPLICATION OF ULTRASOUND TO THE N-ALKYLATION OF AMINES USING PHASE TRANSFER CATALYSIS
The application of ultrasound to the N-alkylation of a variety of amines by alkyl halides under phase transfer conditions (polyethylene glycol methyl ether and alkylammonium compounds as catalysts) leads to a decrease in the time required to effect reaction.
Davidson, R. Stephen,Patel, Ali M.,Safdar, Ali,Thornthwaite, David
p. 5907 - 5910
(1983)
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Organic fluorescent dendrimer thin film material and preparation method thereof
The invention discloses an organic fluorescent dendritic molecular film material and a preparation method thereof, and relates to the technical field of fluorescence sensing. A dendritic molecular main chain skeleton is formed by a central core unit A and
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(2021/03/13)

Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling
A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.
Coote, Michelle L.,Fung, Alfred. K. K.,Sherburn, Michael S.,Yu, Li-Juan
p. 9723 - 9732
(2021/07/20)

Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents
Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 μg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 μg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect.
Xue, Yi-Jie,Li, Ming-Yue,Jin, Xue-Jun,Zheng, Chang-Ji,Piao, Hu-Ri
p. 295 - 306
(2021/01/13)

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
p. 4159 - 4170
(2021/03/09)

Method for synthesizing carbazole derivative
The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.
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(2021/10/05)

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air
An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.
Do, Ha Nam,Quan, Nguyen Minh,Van Phuc, Ban,Van Tinh, Dinh,Tien, Nguyen Quyet,Nga, Truong Thi Thanh,Nguyen, Van Tuyen,Hung, Tran Quang,Dang, Tuan Thanh,Langer, Peter
supporting information
p. 611 - 615
(2021/01/21)

Iridium complex phosphorescent luminescent material and synthesis method thereof
The invention discloses an iridium complex phosphorescent luminescent material and a synthesis method thereof. The iridium complex phosphorescent light-emitting material comprises a thermal excitationdelayed fluorescence unit and an iridium complex phosphorescent light-emitting unit. The iridium complex phosphorescent light-emitting material provided by the invention has relatively high light-emitting efficiency.
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(2020/02/10)

Redox-neutral decarboxylative photocyclization of anthranilic acids
A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
Huang, Huawen,Deng, Kun,Deng, Guo-Jun
p. 8243 - 8247
(2020/12/29)

Synthons for developing organic semiconductors
A process for the synthesis of π-conjugated materials including a step of utilizing a synthon having a carbazole or fluorene nucleus.
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(2019/09/17)

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage
In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.
Chen, Hongyi,Yang, Hongqin,Li, Nutao,Xue, Xinghua,He, Ze,Zeng, Qingle
p. 1679 - 1685
(2019/08/20)

Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates
The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.
Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee
supporting information
p. 4759 - 4763
(2018/08/24)

Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles
A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleo-philic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.
Zhao, Xinxin,Chen, Ming,Huang, Binbin,Yang, Chao,Gao, Yuan,Xia, Wujiong
p. 2981 - 2989
(2018/05/15)

Diversity of metal-organic macrocycles assembled from carbazole based ligands with different lengths
A series of carbazole based ligands with different lengths were assembled with nickel ions to construct metal-organic macrocycles. High-resolution mass spectrometry and ion mobility-mass spectrometry have been used to analyse the resulting MnLn assembly coexisting in solution. Combining with the structural analysis of their solid confirmation, it was revealed that the diversity of the metal-organic macrocycles was increased with the flexibility of the ligands.
Yu, Hao,Wang, Jing,Guo, Xiangyang,Zhang, Rong,He, Cheng,Duan, Chunying
supporting information
p. 4040 - 4044
(2018/03/26)

Synthesis of carbazole derivatives containing chalcone analogs as non-intercalative topoisomerase II catalytic inhibitors and apoptosis inducers
Novel topoisomerase II (Topo II) inhibitors have gained considerable interest for the development of anticancer agents. In this study, a series of carbazole derivatives containing chalcone analogs (CDCAs) were synthesized and investigated for their Topo II inhibition and cytotoxic activities. The results from Topo II mediated DNA relaxation assay showed that CDCAs could significantly inhibit the activity of Topo II, and the structure-activity relationship indicated the halogen substituent in phenyl ring play an important role in the activity. Further mechanism studies revealed that CDCAs function as non-intercalative Topo II catalytic inhibitors. Moreover, some CDCAs showed micromolar cytotoxic activities. The most potent compound 3h exhibited notable growth inhibition against four human cancer cell lines. Flow cytometric analysis revealed that compounds 3d and 3h arrested the HL-60 cells in sub G1 phase by induction of apoptosis. It was further confirmed by Annexin-V-FITC binding assay. Western blot analysis revealed that compound 3h induces apoptosis likely through the activation of caspase proteins.
Li, Peng-Hui,Jiang, Hong,Zhang, Wen-Jin,Li, Yong-Lian,Zhao, Min-Cong,Zhou, Wei,Zhang, Lan-Yue,Tang, Ya-Dong,Dong, Chang-Zhi,Huang, Zhi-Shu,Chen, Hui-Xiong,Du, Zhi-Yun
p. 498 - 510
(2018/01/17)

Synthesis and biological evaluation of novel carbazole-rhodanine conjugates as topoisomerase II inhibitors
In this study, a series of carbazole-rhodanine conjugates was synthesized and evaluated for their Topoisomerase II inhibition potency as well as cytotoxicity against a panel of four human cancer cell lines. Among these thirteen compounds, 3a, 3b, 3g, and
Jiang, Hong,Zhang, Wen-Jin,Li, Peng-Hui,Wang, Jian,Dong, Chang-Zhi,Zhang, Kun,Chen, Hui-Xiong,Du, Zhi-Yun
supporting information
p. 1320 - 1323
(2018/03/21)

Synthesis, photophysical and electrochemical properties of a blue emitter with binaphthalene and carbazole units
A blue emitter, 3,3′-(2,2′-dimethoxy-[1,1′-binaphthalene]-6,6′-diyl)bis(9-benzyl-9H-carbazole), was synthesized by Suzuki coupling reaction. The photophysical properties of the emitter in solution were firstly investigated by UV–Vis absorption and fluorescence emission techniques. The results indicate that the emitter has excellent optical and electron transfer properties. The maximum absorption and emission peaks of the emitter are 302 nm and 406 nm with 67.4% fluorescence quantum yield in chloroform, respectively. Thermal stability study reveals that the emitter has a good thermal stability (Td > 330 °C, Tg > 160 °C). Electrochemical Redox properties of the emitters were measured by cyclic voltammetry, and the energy gaps of highest occupied molecular orbital and the lowest unoccupied molecular orbital levels are in good agreement with the results of theoretical calculation. Furthermore, the multilayer electrochemcial device with the emitter was fabricated and its properties were explored. The wavelength of electroluminescence for the device with this emitter locates at 428 nm. These results indicate the emitter as a deep blue-emitting material has promising application in organic light-emitting diode devices.
Guo, Lixia,Wang, Xiaoju,Feng, Liheng
p. 376 - 381
(2018/05/24)

Dual gold and photoredox catalysed C-H activation of arenes for aryl-aryl cross couplings
A mild and fully catalytic aryl-aryl cross coupling via gold-catalysed C-H activation has been achieved by merging gold and photoredox catalysis. The procedure is free of stoichiometric oxidants and additives, which were previously required in gold-catalysed C-H activation reactions. Exploiting dual gold and photoredox catalysis confers regioselectivity via the crucial gold-catalysed C-H activation step, which is not present in the unselective photocatalysis-only counterpart.
Gauchot,Sutherland,Lee
p. 2885 - 2889
(2017/04/04)

Ruthenium catalyzed remote C4-selective C-H functionalisation of carbazoles: Via σ-activation
We report the C4-selective C-H alkylation of carbazole derivatives furnished with a pyrimidine directing group at N9. This was realized using ruthenium catalyzed σ-activation methodology, whereby C-H activation at C1 enables the interaction of this ruthenacycle, at the para position to the metal center, with tertiary alkyl radicals.
Leitch, Jamie A.,Heron, Callum J.,McKnight, Janette,Kociok-K?hn, Gabriele,Bhonoah, Yunas,Frost, Christopher G.
supporting information
p. 13039 - 13042
(2017/12/15)

Electron-Transfer and Hydride-Transfer Pathways in the Stoltz–Grubbs Reducing System (KOtBu/Et3SiH)
Recent studies by Stoltz, Grubbs et al. have shown that triethylsilane and potassium tert-butoxide react to form a highly attractive and versatile system that shows (reversible) silylation of arenes and heteroarenes as well as reductive cleavage of C?O bonds in aryl ethers and C?S bonds in aryl thioethers. Their extensive mechanistic studies indicate a complex network of reactions with a number of possible intermediates and mechanisms, but their reactions likely feature silyl radicals undergoing addition reactions and SH2 reactions. This paper focuses on the same system, but through computational and experimental studies, reports complementary facets of its chemistry based on a) single-electron transfer (SET), and b) hydride delivery reactions to arenes.
Smith, Andrew J.,Young, Allan,Rohrbach, Simon,O'Connor, Erin F.,Allison, Mark,Wang, Hong-Shuang,Poole, Darren L.,Tuttle, Tell,Murphy, John A.
supporting information
p. 13747 - 13751
(2017/10/12)

Novel carbazole skeleton-based photoinitiators for led polymerization and LED projector 3D printing
Radical chemistry is a very convenient way to produce polymer materials. Here an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides utilizing Light Emitting Diodes LEDs @405 nm. Excellent polymerization-initiating abilities are found and high final reactive function conversions are obtained. Interestingly, these new derivatives display much better near-UV polymerization-initiating abilities compared to a reference UV absorbing carbazole (CARET 9H-carbazole-9-ethanol) demonstrating that the new substituents have good ability to red shift the absorption of the proposed photoinitiators. All the more strikingly, in combination with iodonium salt, Cd1–Cd7 are likewise preferred as cationic photoinitiators over the notable photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO) for mild irradiation conditions featuring their remarkable reactivity. In particular their utilization in the preparation of new cationic resins for LED projector 3D printing is envisioned. A full picture of the included photochemical mechanisms is given.
Mousawi, Assi Al,Garra, Patxi,Dumur, Frédéric,Bui, Thanh-Tuan,Goubard, Fabrice,Toufaily, Joumana,Hamieh, Tayssir,Graff, Bernadette,Gigmes, Didier,Fouassier, Jean Pierre,Lalevée, Jacques
supporting information

(2018/01/12)

A Novel and Chemoselective Process of N -Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material
The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.
González-González, Carlos A.,Vega, Juan Javier Mejía,Monroy, Ricardo García,González-Calderón, Davir,Corona-Becerril, David,Fuentes-Benítes, Aydeé,Mascarúa, Joaquín Tamariz,González-Romero, Carlos
(2018/02/28)

A by a process for preparing amine derivatives of green method (by machine translation)
The invention discloses a by a process for preparing amine derivatives of green method, dumping with amine compound in a non-transition metal catalyst under solvent-free conditions and through the controllable high selection dehydration alkylation reaction different amine derivatives, a non-transition metal catalyst is a halogenated hydrocarbon, halogenated hydrocarbon in an amount of 1 - 50 μM %, under the catalysis of the mellow and amine in halogenated hydrocarbon can be directly performed by the amine derivative dehydration reaction, the reaction temperature is 100 - 180 °C, the reaction time is 12 - 48 hours, the by-product is water, the reaction needs to be carried out under the protection of inert gas, simple conditions, easy to operate, the by-product is water, the reaction selectivity is controllable, the target high selectivity. Requirements for reaction condition of relatively low, primary and secondary alcohol can be used for the alkylation reagent, is suitable for the dehydration of the primary and secondary amines single alkylation reaction, is also suitable for the dehydration of the double alkylation reaction of a primary amine, with wider scope, should also has certain research and industrial application prospect. (by machine translation)
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(2017/08/14)

Substituted Carbazoles-A New Class of Anthelmintic Agent
A series of novel carbazoles were synthesized based on structural modifications to lead carbazole 1 (EC100≤2.5M against Haemonchus contortus in vitro), which was revealed in a small molecule screening program as a potentially promising platform for the development of new anthelmintic drugs. Subsequently, analogues 19, 21, 41, 42 (EC100≤ 1.25M, all), and 39 (EC100≤0.625M) were demonstrated to exhibit enhanced in vitro anthelmintic activity over the lead structure, with compound 39 also being shown to be active in vivo against Heligmosomoides polygyrus.
Rennison, David,Gueret, Stephanie M.,Laita, Olivia,Bland, Ross J.,Sutherland, Ian A.,Boddy, Ian K.,Brimble, Margaret A.
p. 1268 - 1276
(2016/11/25)

Compound containing benzoxazole and carbazole constitutional units and application thereof
The invention discloses a compound 1,1-di(benzoxazole-2-yl)-2-(N-benzyl carbazole-2-yl) ethylene containing benzoxazole and carbazole constitutional units and the application thereof. The molecular structural formula of the compound 1,1-di(benzoxazole-2-y
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(2016/10/07)

Selective catalytic Hofmann: N -alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides
Using only catalytic amounts of alkyl halides in the reactions of poor nucleophilic amines/amides and alcohols led to a selective Hofmann N-alkylation reaction catalytic in alkyl halides, providing a practical and efficient method for the practical synthesis of mono- or di-alkylated amines/amides in high selectivities. This new method avoids the use of large amounts of bases, alkyl halides, and solvents, and generates water as the only byproduct. Preliminary mechanistic studies showed that alkyl halides are key intermediates/catalysts regeneratable in the reaction cycle.
Xu, Qing,Xie, Huamei,Zhang, Er-Lei,Ma, Xiantao,Chen, Jianhui,Yu, Xiao-Chun,Li, Huan
supporting information
p. 3940 - 3944
(2016/07/21)

Synthesis of Carbazole Alkaloids by Ring-Closing Metathesis and Ring Rearrangement-Aromatization
Aprocess for the assembly of carbazole alkaloids has been developed on the basis of ring-closing metathesis (RCM) and ringrearrangement-aromatization (RRA) as the key steps. This method is based on allyl Grignard addition to isatin derivatives to provide smooth access to 2,2-diallyl 3-oxindole derivatives through a 1,2-allyl shift. The diallyl derivatives were used as RCM precursors to afford a novel class of spirocyclopentene-3-oxindole derivatives, which underwent a novel RRA reaction to afford carbazole derivatives. The synthetic sequence to carbazoles was shortened by combining the RCM and RRA steps in an orthogonal tandem catalytic process. The utility of this methodology was further demonstrated by the straightforward synthesis of carbazole alkaloids, including amukonal derivative, girinimbilol, heptaphylline, and bis(2-hydroxy-3-methylcarbazole). Just a hop, skip, and a jump away: The addition of allyl Grignard/indium reagents to isatins, ring-closing metathesis (RCM), and ring rearrangement-aromatization (RRA) provided carbazole derivatives in high overall yield (see scheme). The RCM step afforded spirocyclic 3-oxindoles, which underwent acid-catalyzed RRA to give carbazoles. A step-economical tandem RCM/RRA process was also developed and applied to the synthesis of carbazole alkaloids.
Dhara, Kalyan,Mandal, Tirtha,Das, Joydeb,Dash, Jyotirmayee
p. 15831 - 15835
(2016/01/29)

A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides
The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.
Kim, So Han,Kim, Min,Verkade, John G.,Kim, Youngjo
p. 1954 - 1960
(2015/03/18)

COMPOUND, LIGHT-EMITTING MATERIAL, AND ORGANIC LIGHT-EMITTING ELEMENT
The compound represented by the following general formula is useful as a light emitting material. Ar 1 represents an arylene group, Ar 2 and Ar 3 represent an aryl group, and R 1 to R 8 represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 8 represents a diarylamino group.
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(2016/11/14)

An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine
Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
Zhao, Sanhu,Kang, Jin,Du, Yuting,Kang, Jingyan,Zhao, Xiaoni,Xu, Yinfeng,Chen, Ruixi,Wang, Qianqian,Shi, Xitao
supporting information
p. 683 - 689
(2014/06/10)

Aggregation-induced emission, mechanochromism and blue electroluminescence of carbazole and triphenylamine-substituted ethenes
Carbazole and triphenylamine-substituted ethenes are synthesized [Ph 2CCPh(R), R = 9-carbazolyl, 9-hexyl-3-carbazolyl and 4-(diphenylamino)phenyl] and their optical properties are investigated. All luminogens are nonemissive when molecularly dissolved in good solvents but become highly emissive in the aggregated state, showing a phenomenon of aggregation-induced emission. High solid-state fluorescence quantum yields up to 97.6% have been achieved in their solid thin films. The luminogens are thermally stable, showing high degradation temperatures of up to 315 °C. They exhibit mechanochromism: their emissions can be repeatedly switched between blue and green colors by simple grinding-fuming and grinding-heating processes due to the morphological change from crystalline to amorphous state and vice versa. Multilayer light-emitting diodes with device configurations of ITO/NPB/dye/TPBi/Alq3/LiF/Al, ITO/NPB/dye/TPBi/LiF/Al and ITO/dye/TPBi/LiF/Al are fabricated, which emit sky blue light with maximum luminance, current efficiency, power efficiency and external quantum efficiency of 11700 cd m-2, 7.5 cd A-1, 7.9 lm W-1 and 3.3%, respectively.
Chan, Carrie Y. K.,Lam, Jacky W. Y.,Zhao, Zujin,Chen, Shuming,Lu, Ping,Sung, Herman H. Y.,Kwok, Hoi Sing,Ma, Yuguang,Williams, Ian D.,Tang, Ben Zhong
p. 4320 - 4327
(2014/06/09)

Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: A combined experimental and computational investigation
A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups. This journal is the Partner Organisations 2014.
Humne, Vivek,Dangat, Yuvraj,Vanka, Kumar,Lokhande, Pradeep
p. 4832 - 4836
(2014/07/07)

Syntheses and QSAR studies of benzylimidazole derivatives and benzylcarbazole as potential aromatase inhibitors
In this study, in order to explore new structures and chemical entities as aromatase inhibitors, benzylcarbazole, 12 benzylimidazole derivatives with different substituents on both phenyl and imidazole rings were synthesized and their aromatase inhibitory were evaluated with fluorescent substrate detection method. The results showed that the compounds with carboxyl and ester groups in phenyl ring show better inhibitory activity. The introduction of alkyl groups in imidazole may improve the aromatase inhibitory activity. Most of the compounds were more potent than aminoglutethimide and tamoxifen. 2-[2-{(2-ethyl-4-methyl- 1H-imidazol-1-yl)methyl}phenyl]acetic acid and benzylcarbazole have the highest bioactivities with IC50 values of 6.19 μM and 2.72 μM respectively. A meaningful QSAR model with LOF = 0.00359, R2 = 0.9914, Adj-R 2 = 0.9853, R2cv = 0.9639, F = 161.8, was constructed with genetic functional algorithm using discovery studio 2.1 package.
Dai,Xiao,Wang,Wei,Zhang,Ma,Zheng,Hou,Zhang
p. 2381 - 2388
(2014/06/09)

Diazadioxa[8]circulenes: Planar antiaromatic cyclooctatetraenes
In this paper we describe a new class of antiaromatic planar cyclooctatetraenes: the diazadioxa[8]circulenes. The synthesis was achieved by means of a new acid-mediated oxidative dimerization of 3,6-dihydroxycarbazoles to yield the diazadioxa[8]circulenes
Hensel, Thomas,Trpcevski, Denis,Lind, Christopher,Grosjean, Remi,Hammershoj, Peter,Nielsen, Christian B.,Brock-Nannestad, Theis,Nielsen, Bjarne E.,Schau-Magnussen, Magnus,Minaev, Boris,Baryshnikov, Gleb V.,Pittelkow, Michael
p. 17097 - 17102
(2014/01/06)

Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts
The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues.
Riedmueller, Stefan,Nachtsheim, Boris J.
p. 1202 - 1209
(2013/07/26)

Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents
By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.
Sueki, Shunsuke,Kuninobu, Yoichiro
supporting information
p. 1544 - 1547
(2013/06/26)

A blue emission polymer: Synthesis, photophysical and electrochemical properties
(Figure Presented) A novel π-conjugated polymer (PCPyrene) containing N-benzylcarbazole and pyrene units has been synthesized and characterized. The polymer possesses high thermal stability with the decomposition temperature of 440°C. It shows higher fluorescence quantum yields of in solution and solid state, respectively. PCPyrene can emit bright blue-lights both in different organic solutions (440-460 nm) and in the solid state (492 nm). Compared the emission spectra of PCPyrene in solutions with in solid state, the solid state emission of PCPyrene is significantly red-shifted. Additionally, it is not obvious changes of the solid emission spectra even after being annealed at 150°C under nitrogen for 24 h. The electrochemical properties and energy levels of PCPyrene were also investigated by cyclic voltammetry. Furthermore, in order to provide a basis forecasting the structure-physical property relationships, the photophysical properties of PCPyrene have been carefully investigated by fluorescence emission and UV-vis absorption spectra.
Zhang, Caihong,Li, Feng,Wang, Yue,Feng, Liheng
p. 159 - 163
(2014/01/23)

Reductive cleavage of amides to alcohols and amines catalyzed by well-defined bimetallic molybdenum complexes
Triple bonds do it! The molybdenum-catalyzed Ci-N bond cleavage of organic amides with hydrosilanes to produce alcohols and amines has been investigated. This work complements previously established protocols that lead to the cleavage of the Ci-O bond. Modified triply bonded dimolybdenum(III) alkoxides have been found to be crucial for tuning the selectivity to Ci-N bond cleavage (see figure). Copyright
Krackl, Sebastian,Someya, Chika I.,Enthaler, Stephan
supporting information
p. 15267 - 15271
(2013/01/15)

Experimental and theoretical studies on the one-photon and two-photon properties of a series of carbazole derivatives containing styrene
Symmetric-type carbazole derivatives show great potential for application in two-photon absorption (TPA) materials and organic light-emitting diodes. The absorption spectra and fluorescence emission spectra of three different N-alkyl symmetric-type carbazole derivatives were investigated. The density functional theory (DFT) time-dependent-DFT//Becke, three-parameter, Lee-Yang-Parr/6- 31G* method has been used to theoretically study one-photon absorption properties. The computational results are in good agreement with the available experimental values. The two-photon excited fluorescence of the compounds was surveyed by 120fs pulse at 790nm Ti: sapphire laser operating at 1kHz repetition rate. Two-photon excited fluorescence was obtained in the range of 380-600nm, and TPA cross-sections were calculated. The TPA properties of the series of compounds were investigated by the ZINDO/single and double electronic excitation configuration interaction method. The influence of the chemical structure of the compounds on two-photon optical properties was discussed. The results show how the different changes in one-photon absorption and TPA properties on the basis of lengthening the conjugated bridge and the different carbazole N-alkyl substituents are attributed to the transition dipole moment in the excited process. Copyright
Li, Liang,Wu, Yiqun,Zhou, Qinling,He, Chunying
experimental part
p. 362 - 372
(2012/07/28)

Carbazole inhibitors of histamine receptors for the treatment of disease
The present invention relates to carbazole compounds, pharmaceutical compositions comprising them, and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.
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Page/Page column 41

(2012/01/04)

BISTABLE CARBAZOLE COMPOUNDS
Bistable carbazole compounds of formula (I) are described, wherein M is Fe, Co, Ru or Os, preferably Fe, useful as basic functional units for computing systems based on the QCA (Quantum Cellular Automata) paradigm; a process for their preparation is also
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(2011/07/08)

Synthesis and photophysics of dibenz[a,c]phenazine derivatives
The synthesis of dipolar dibenz[a,c]phenazine (DBP) derivatives is described. The compounds possess little electronic communication between donor and acceptor units in the ground state regardless of the pattern of substitution. The dipolar derivatives deactivate mostly via electron transfer (eT) under polar conditions. Intersystem crossing is likely to compete for S1 relaxation.
Estrada, Leandro A.,Neckers, Douglas C.
supporting information; experimental part
p. 3304 - 3307
(2011/09/15)

Highly efficient ligands for the palladium-assisted double N-arylation of primary amines for one-sep construction of carbazoles
A highly efficient one-pot synthesis of carbazoles via palladium-catalyzed double N-arylation of primary amines with 2,2'-dihalobiphenyls is described using a catalyst system comprised of tris(dibenzylideneacetone)dipalladium(O) (Pd2dba3) and the proazaphosphatrane P(i-BuNCH 2CH2)3N (8) or its derivative (t-Bu) 2P=N-P(iBuNCH2CH2)3N (9a) as the ligand. The process is effective for double N-arylation of 2,2'-biphenyl dibromide, diiodide, and even dichloride with a variety of primary amines including neutral, electronrich, electron-deficient, and sterically hindered anilines as well as aliphatic amines.
Zhou, Yibo,Verkade, John G.
supporting information; experimental part
p. 616 - 620
(2010/07/03)

Solid-liquid phase alkylation of n-heterocycles: Microwave-assisted synthesis as an environmentally friendly alternative
The solid-liquid phase alkylation of a variety of five-membered N-heterocycles (carbazole, imidazole, benzimidazole, and indole-3-carbaldehyde) was carried out under different conditions. The use of alkali carbonate in dimethylformamide or in MeCN (in the latter case, in the presence of a phase-transfer catalyst) is a suitable method to prepare the corresponding N-alkylated products in an efficient way. In most cases, the solventless, microwave-assisted reaction is an environmentally friendly alternative to traditional methods. Copyrigh
Milen, Matyas,Gruen, Alajos,Balint, Erika,Dancso, Andras,Keglevich, Gyoergy
experimental part
p. 2291 - 2301
(2010/09/17)

BISTABLE CARBAZOLE COMPOUNDS
Bistable carbazole compounds of formula (I) are described, wherein M is Fe, Co, Ru or Os, preferably Fe, useful as basic functional units for computing systems based on the QCA (Quantum Cellular Automata) paradigm; a process for their preparation is also
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Page/Page column 10

(2010/04/06)

HOST MATERIAL FOR LIGHT-EMITTING DIODES
The present invention relates to a host material comprising a compound having two carbazole moieties which is suitable for blue-emitting OLEDs. Surprisingly, it has been found that when appropriate substituents are present in the carbazole structure, the solubility of the compounds can be improved without any adverse effect on the OLED performance. The present invention further relates to the use of the host materials and to an organic light emitting device comprising the host material.
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(2010/04/30)

Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature
We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems. The catalytic amination process operates under extremely mild conditions and produces carbazole products in good to excellent yields. Carbazoles possessing complex molecular architecture can also be formed using this reaction, highlighting its potential in natural product synthesis applications. Preliminary mechanistic investigations reveal the reaction proceeds through a Pd(II)/Pd(IV) manifold and that reductive elimination from a high oxidation state Pd(IV) complex facilitates the mild conditions of this transformation. Copyright
Jordan-Hore, James A.,Johansson, Carin C. C.,Gulias, Moises,Beck, Elizabeth M.,Gaunt, Matthew J.
supporting information; experimental part
p. 16184 - 16186
(2009/05/08)

3-Aminocarbazole Compounds, Pharmaceutical Composition Containing the Same and Method for the Preparation Thereof
A compound of formula (I), in which R1, R2, R3, R4, R5, R6, X and Y have the meanings indicated in the description, and the pharmaceutically acceptable salts thereof. A pharmaceutical composition containing a compound of formula (I) or a pharmaceutically acceptable salt thereof. A method for preparing the abovementioned compound of formula (I) and the pharmaceutically acceptable salts thereof.
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Page/Page column 5

(2008/12/08)

3-AMINOCARBAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AND METHOD FOR THE PREPARATION THEREOF
A compound of formula (I), in which R1 , R2, R3, R4, R5, R6, X and Y have the meanings indicated in the description, and the pharmaceutically acceptable salts thereof. A pharmaceutical composition containing a compound of formula (I) or a pharmaceutically acceptable salt thereof. A method for preparing the abovementioned compound of formula (I) and the pharmaceutically acceptable salts thereof.
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Page/Page column 14-15

(2010/11/25)