- Hole-transporting side-chain polystyrenes based on TCTA with tuned glass transition and optimized electronic properties
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The development of crosslinkable materials for the fabrication of solution processable OLEDs presents challenges, especially regarding the adjustment of the glass transition (Tg), which has a significant influence on crosslinking kinetics and d
- Limberg, Felix R. P.,Miasojedovas, Arunas,Pingel, Patrick,Reisbeck, Felix,Janietz, Silvia,Monkman, Andrew P.,Krüger, Hartmut
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Read Online
- Preparation method of carbazole and fluorene organic electroluminescent intermediates
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The invention discloses a preparation method of a carbazole and fluorene organic electroluminescent intermediate. The preparation method comprises the following steps: taking bromo-carbazole, fluorene or a derivative thereof and alkyl alcohol as raw mater
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Paragraph 0041-0044
(2021/07/14)
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- Visible-light-driven Cadogan reaction
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Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
- Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
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supporting information
p. 2582 - 2586
(2021/03/09)
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- NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
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A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.
- Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
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supporting information
p. 5349 - 5353
(2021/07/21)
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- ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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An organometallic compound and an organic light-emitting device including the same.
- -
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Paragraph 0390; 0393-0394
(2020/06/16)
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- Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions
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Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.
- Akiyama, Toshiki,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Hasegawa, Jun-Ya,Honma, Tetsuo,Mashima, Kazushi,Sato, Yoshihiro,Shimoda, Shuhei,Shio, Yasunori,Suzuki, Takeyuki,Tamenori, Yusuke,Tsurugi, Hayato,Tsuruta, Kazuki,Wada, Yuki,Yamada, Makito
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supporting information
p. 7244 - 7249
(2020/10/12)
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- Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents
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A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.
- Bhattacharjee, Argha,Hosoya, Hiromu,Ikeda, Hideaki,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi
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p. 11278 - 11282
(2018/10/20)
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- Visible-light-promoted intramolecular C-H amination in aqueous solution: Synthesis of carbazoles
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An effective and operationally simple protocol is reported for the synthesis of versatile carbazoles. With water as a co-solvent, visible-light rather than various metals is used to facilitate the conversion of readily available 2-azidobiphenyls under mild conditions. Various functionalized bioactive natural alkaloids, such as glycoborine, clausine C, clausine L, clausine H and clauszoline K, were synthesized efficiently with nitrogen as a sole byproduct. The reaction could be performed in water, acidic or alkaline buffer solutions, showing its potential for applications in biochemistry.
- Yang, Lizheng,Zhang, Yipin,Zou, Xiaodong,Lu, Hongjian,Li, Guigen
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supporting information
p. 1362 - 1366
(2018/03/26)
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- Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole
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A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.
- Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng
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supporting information
p. 216 - 219
(2018/01/17)
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- Carbazole compound, and synthesis method and application of compound
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The invention discloses a carbazole compound represented by a formula (2) and a synthesis method of the compound. A high-iodine salt is taken as a reaction raw material, and under the action of an inorganic nitrogen reagent, an additive, a base and a metal catalyst, a reaction is carried out in a solvent under a condition of 80-150 DEG C to obtain various carbazole compounds. According to the method provided by the invention, nitrogen atoms are introduced in a later period, so that the non-compatibility of nitrogen heterocyclic rings to the reaction conditions such as the metal catalyst and the like in an early reaction period is avoided. In addition, two aryl groups in the high-iodine salt are fully utilized, so that the atomic economic efficiency of the method provided by the present invention is fully exhibited. The carbazole compound prepared by the method provided by the invention can be further applied to the synthesis of non-steroidal anti-inflammatory drug carprofen.
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-
Paragraph 0042-0045
(2018/06/15)
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- Tuning the ambipolar charge transport properties of tricyanovinyl-substituted carbazole-based materials
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A series of push-pull carbazole-based compounds has been experimentally and theoretically characterized in combination with the X-ray analysis of the corresponding single crystals. The introduction of the strong electron-withdrawing tricyanovinyl group in the carbazole core affords electron-transporting ability in addition to the characteristic hole-transporting properties exhibited by donor carbazole derivatives.
- Reig, Marta,Bagdziunas, Gintautas,Volyniuk, Dmytro,Grazulevicius, Juozas V.,Velasco, Dolores
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p. 6721 - 6730
(2017/08/17)
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- Photochemical intramolecular amination for the synthesis of heterocycles
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Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.
- Parisien-Collette, Shawn,Cruché, Corentin,Abel-Snape, Xavier,Collins, Shawn K.
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supporting information
p. 4798 - 4803
(2017/10/23)
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- A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A
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The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.
- Yan, Qiao,Gin, Emma,Wasinska-Kalwa, Malgorzata,Banwell, Martin G.,Carr, Paul D.
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p. 4148 - 4159
(2017/04/27)
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- Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate
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A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.
- Chatterjee, Tanmay,Roh, Geum-Bee,Shoaib, Mahbubul Alam,Suhl, Chang-Heon,Kim, Jun Soo,Cho, Cheon-Gyu,Cho, Eun Jin
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p. 1906 - 1909
(2017/04/11)
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- Synthetic method of carbazole and derivatives thereof
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The invention discloses a synthetic method of carbazole and derivatives thereof. The synthetic method is characterized in that the carbazole and derivatives thereof are obtained by N-substituted reaction, vinylation reaction, removal of R2 group and olefin closed-loop double decomposition reaction. According to the synthetic method of the carbazole and derivatives thereof, disclosed by the invention, various derivatives of the carbazole can be synthesized according to substituent groups on indole rings of raw materials; in addition, no substituent group is formed on N of the carbazole; the substituent group can be used as an intermediate as required for next-step synthesis. Meanwhile, according to the synthetic method disclosed by the invention, the carbazole and derivatives thereof are synthesized by using the raw materials with abundant sources, and further the huge demand of the carbazole and derivatives thereof is met. Besides, a synthetic route is simple, reaction conditions are easily controlled and realized, the yield of a product is high, and higher practicality is realized.
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Paragraph 0070; 0071; 0072; 0073; 0074; 0075; 0094-0099
(2017/07/18)
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- Ligand- and Base-Free Access to Diverse Biaryls by the Reductive Coupling of Diaryliodonium Salts
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A ligand- and base-free, Pd-catalyzed protocol to access a wide range of symmetrical and unsymmetrical biaryls from stable diaryliodonium salts was developed. The reaction involved the use of an effective and recyclable Pd/polyethylene glycol-400 catalyst system to harness the aryl moieties of two diaryliodonium salts; the ensuing biaryls may be utilized to synthesize an array of useful compounds, including 5-aryluracils, carbazoles, chromenones, fluorenones, phenathridines, and boscalid analogues.
- Arun,Reddy, P. O. Venkataramana,Pilania, Meenakshi,Kumar, Dalip
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supporting information
p. 2096 - 2100
(2016/05/09)
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- Organic electroluminescent materials and devices
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Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.
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Page/Page column 186-187
(2016/10/27)
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- Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C–H Activation and C–N Bond Formation
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An efficient method for the synthesis of the carbazole scaffold was designed and investigated. The method was developed to produce substituted carbazoles by an intramolecular combination of a free amine group and an arene. The steps of the method involved tandem Pd-catalyzed C–H activation and intramolecular C–N bond formation. The method showed good functional group tolerance, and substituent(s) could be on either of the two rings or on both of the two rings of the 2-aminobiphenyl substrate. After ring closure, the reduced Pd catalyst was oxidized to PdIIby hydrogen peroxide. The novel method was also demonstrated to operate excellently with the corresponding 2-N-acetylaminobiphenyls.
- Bj?rsvik, Hans-René,Elumalai, Vijayaragavan
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p. 5474 - 5479
(2016/11/25)
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- Palladium-Catalyzed Intramolecular C–H Amination in Water
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Palladium(II) catalysis was found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic solvents that were investigated.
- Yang, Lizheng,Li, Hao,Zhang, Haifei,Lu, Hongjian
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supporting information
p. 5611 - 5615
(2016/12/14)
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- Iron-Catalyzed Intramolecular C(sp2)-H Amination
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The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
- Alt, Isabel T.,Plietker, Bernd
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supporting information
p. 1519 - 1522
(2016/02/14)
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- TETRADENTATE AND OCTAHEDRAL METAL COMPLEXES CONTAINING NAPHTHYRIDINOCARBAZOLE AND ITS ANALOGUES
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Tetradentate and octahedral metal complexes suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.
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Paragraph 0284; 0285
(2016/12/26)
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- Palladium on Carbon-Catalyzed C?H Amination for Synthesis of Carbazoles and its Mechanistic Study
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10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C?H amination of various N-mesylated 2-aminobiphenyls in the presence of a catalytic amount of pyridine N-oxide in heated dimethyl sulfoxide (DMSO) under an oxygen atmosphere to afford the corresponding N-mesylcarbazoles. The reaction would proceed via a single-electron transfer process based on its significant suppression by the addition of a single-electron scavenger, tetracyanoquinodimethane (TCNQ), and the substituents on the aromatic rings of the substrate have an insignificant effect on the reaction progress. (Figure presented.).
- Monguchi, Yasunari,Okami, Hiroki,Ichikawa, Tomohiro,Nozaki, Kei,Maejima, Toshihide,Oumi, Yasunori,Sawama, Yoshinari,Sajiki, Hironao
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supporting information
p. 3145 - 3151
(2016/10/09)
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- One-pot synthesis of carbazoles via tandem C-C cross-coupling and reductive amination
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We have developed a highly efficient synthetic route to carbazoles that employs sequential C-C/C-N bond formation via Suzuki cross-coupling and Cadogan cyclization using commercially available or easily preparable starting materials. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products (glycozoline, glycozolicine, glycozolidine and clausenalene).
- Goo, Deuk-Young,Woo, Sang Kook
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supporting information
p. 122 - 130
(2015/12/30)
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- Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
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The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
- Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 1597 - 1600
(2015/03/30)
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- Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
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A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
- Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 2892 - 2895
(2014/06/23)
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- A tandem reduction-oxidation protocol for the conversion of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoles via tosylhydrazones through microwave assistance: Efficient synthesis of glycozoline, clausenalene, glycozolicine, and deoxycarbazomycin B and the total synthesis of murrayafoline A
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A novel and efficient methodology for the synthesis of carbazoles from 1-keto-1,2,3,4-tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one-pot tandem reduction-oxidation protocol using a combination of NaBH4 and Pd-C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3-methylcarbazole, glycozoline, clausenalene, glycozolicine, murrayafoline A, and deoxycarbazomycin B, a carbazole derivative that is known to have a promising antimicrobial activity.
- Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
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- Recyclable copper catalyzed nitrogenation of biphenyl halides: A direct approach to carbazoles
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A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.
- Ou, Yang,Jiao, Ning
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supporting information
p. 3473 - 3475
(2013/05/22)
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- Reactions of arynes with nitrosoarenes - An approach to substituted carbazoles
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No transition metals are necessary in the reaction of in situ generated arynes with nitrosoarenes to give substituted carbazoles. Depending on the fluoride source and the solvent, either N-arylated carbazoles or NH-carbazoles are obtained (see scheme; DME=dimethoxyethane, OTf=trifluoromethanesulfonate). In these cascades a C-C and one or two C-N bonds are formed. The reactions are easy to conduct and proceed under mild conditions. Copyright
- Chakrabarty, Shyamal,Chatterjee, Indranil,Tebben, Ludger,Studer, Armido
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p. 2968 - 2971
(2013/03/29)
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- Amino-directed RhIII-catalyzed C-H activation leading to one-pot synthesis of N-H carbazoles
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One-pot synthesis: An efficient amino-directed one-pot synthesis of N-H carbazoles from unprotected 2-aminobiaryl compounds is reported. The free amino unit acts as both a directing group for ortho C-H activation and a functional group for construction of an N-heterocyclic ring (see scheme). Copyright
- Jiang, Qibai,Duan-Mu, Dandan,Zhong, Wei,Chen, Hao,Yan, Hong
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supporting information
p. 1903 - 1907
(2013/03/28)
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- Highly chemoselective Mono-Suzuki arylation reactions on all three dichlorobenzene isomers and applications development
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A Pd catalyst system is described that allows very high chemoselective monoarylation on all three isomers of dichlorobenzene. Direct application of these commodity chemicals to high-value ligands, anilines, azides, and carbazoles was achieved through this process discovery.
- Ullah, Ehsan,McNulty, James,Robertson, Al
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supporting information; experimental part
p. 2127 - 2131
(2012/06/01)
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- Liquid triarylamines: The scope and limitations of piers-rubinsztajn conditions for obtaining triarylamine-siloxane hybrid materials
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New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.
- Kamino, Brett A.,Mills, Bridget,Reali, Christopher,Gretton, Michael J.,Brook, Michael A.,Bender, Timothy P.
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p. 1663 - 1674
(2012/04/17)
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- Kinesin spindle protein (KSP) inhibitors with 2,3-fused indole scaffolds
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Mitotic kinesin spindle protein (KSP) is involved in the assembly of the bipolar spindle during cell division. On the basis of a common 2,3-fused indole substructure within the complex frameworks of terpendole E and other KSP inhibitors, the carbazoles with a bulky alkyl group were identified as a novel KSP inhibitory scaffold. Additionally, among several naturally occurring cell growth inhibitors with 2,3-fused indole structures,β-carboline alkaloids, harman and harmine, showed moderate inhibition of KSP.
- Oishi, Shinya,Watanabe, Toshiaki,Sawada, Jun-Ichi,Asai, Akira,Ohno, Hiroaki,Fujii, Nobutaka
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experimental part
p. 5054 - 5058
(2010/09/05)
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- Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine
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A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.
- Sridharan, Vellaisamy,Antonia Martin,Carlos Menendez
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supporting information; experimental part
p. 4614 - 4621
(2009/12/05)
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- Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: Synthesis and mechanistic study
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(Chemical Equation Presented) An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.
- Watanabe, Toshiaki,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
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experimental part
p. 4720 - 4726
(2009/10/02)
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- Rh2(II)-catalyzed synthesis of carbazoles from biaryl azides
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An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.
- Stokes, Benjamin J.,Jovanovic, Brankica,Dong, Huijun,Richert, Kathleen J.,Riell, Ryan D.,Driver, Tom G.
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supporting information; experimental part
p. 3225 - 3228
(2009/08/07)
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- Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: Reaction development and scope
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(Figure Presented) New reaction conditions for intramolecular palladium(II)-catalyzed oxidative carbon-carbon bond formation under air are described. The use of pivalic acid as the reaction solvent, instead of acetic acid, results in greater reproducibility, higher yields, and broader scope. This includes the use of electron-rich diarylamines as illustrated in the synthesis of three naturally occurring carbazole products: Murrayafoline A, Mukonine, and Clausenine. A variety of side products have also been isolated, casting light on competing reaction pathways and revealing new reactivity with palladium(II) catalysis.
- Liegault, Benoit,Lee, Doris,Huestis, Malcolm P.,Stuart, David R.,Fagnou, Keith
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p. 5022 - 5028
(2008/09/21)
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- 9,9'- AND 2,2'-SUBSTITUTED 3,3'-BICARBAZOLYL DERIVATIVES FOR USE IN SEMICONDUCTING MATERIALS AS A HOST MATRIX FOR PHOSPHORESCENT EMITTERS
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The present invention relates to carbazole compounds of formula (I) and a semiconducting material comprising such carbazole compounds. It also relates to a process for the preparation of such carbazole compounds, as well as to the use thereof as a semicon
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Page/Page column 11; 12
(2008/12/05)
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- Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
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An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
- Liu, Zhijian,Larock, Richard C.
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p. 347 - 355
(2007/10/03)
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- Dioxomolybdenum(VI)-catalyzed reductive cyclization of nitroaromatics. Synthesis of carbazoles and indoles
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Reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles, respectively, is carried out by triphenylphosphine under mild conditions catalyzed by a dichlorodioxomolybdenum(VI) complex. A one-pot procedure for the synthesis of regioselectively functionalized indoles has been developed from commercially available onitrobenzaldehydes and phosphoranes.
- Sanz, Roberto,Escribano, Jaime,Pedrosa, Maria R.,Aguado, Rafael,Arnaiz, Francisco J.
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p. 713 - 718
(2008/02/09)
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- Synthesis of oxygenated carbazoles by palladium-mediated oxidative double C-H activation of diarylamines assisted by microwave irradiation
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Microwave irradiation in the presence of palladium acetate and traces of dimethylformamide allows the fast and efficient cyclodehydrogenation of diphenylamines into carbazoles. The scope of the microwave-assisted reaction is broader than that of the one using conventional conditions in that it allows the preparation of oxygenated carbazoles without apparent loss in yield. The applicability of the method to the preparation of carbazole alkaloids has been demonstrated by the development of a total synthesis of murrayafoline A, which proceeds in 50% overall yield from commercially available materials and is the shortest and most efficient route for the preparation of this alkaloid to date. Georg Thieme Verlag Stuttgart.
- Sridharan, Vellaisamy,Martín, Ma. Antonia,Menéndez, J. Carlos
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p. 2375 - 2378
(2008/02/09)
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- OPHTHALMIC COMPOSITIONS FOR TREATING OCULAR HYPERTENSION
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This invention relates to potent potassium channel blocker compounds of Formula I or a formulation thereof for the treatment of glaucoma and other conditions which leads to elevated intraoccular pressure in the eye of a patient. This invention also relates to the use of such compounds to provide a neuroprotective effect to the eye of mammalian species, particularly humans.
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Page/Page column 14 - 15
(2008/06/13)
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- Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems
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A microwave-enhanced Suzuki-Miyaura cross-coupling reaction in combination with a microwave-assisted Cadogan reductive cyclization is presented as an easy access to a variety of 2-substituted carbazoles and other fused heterocyclic systems. Microwave irradiation was found very useful in minimizing the proto-deboronation issues in the cross-coupling reaction, and enhances the rate of reductive cyclization in a dramatic manner.
- Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim
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p. 127 - 133
(2007/10/03)
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- Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles
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The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products.
- Freeman, Adam W.,Urvoy, Marie,Criswell, Megan E.
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p. 5014 - 5019
(2007/10/03)
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- Catalytic C-H Functionalization Driven by CO as a Stoichiometric Reductant: Application to Carbazole Synthesis
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(Equation presented) A palladium-catalyzed regioselective C-H bond functionalization driven by CO as the stoichiometric reductant is described. Nitrogen heterocycles, e.g., carbazoles, are accessible in good to excellent yields with use of palladium acetate and 70 psig of carbon monoxide at 140°C.
- Smitrovich, Jacqueline H.,Davies, Ian W.
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p. 533 - 535
(2007/10/03)
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- Stille and suzuki cross coupling reactions of o-nitrophenyl triflates: A versatile route to a variety of heterocycles
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The cross coupling reactions of selected o-nitrophenyl triflates with arylstannane and arylboron substrates are reported. The resultant 2-nitrobiphenyls provide ready access to a variety of substituted heterocycles.
- Holzapfel, Cedric W.,Dwyer, Catherine
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p. 1513 - 1518
(2007/10/03)
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- Antioxidant activities of phenothiazines and related compounds: Correlation between the antioxidant activities and dissociation energies of O-H or N-H bonds
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The antioxidant activities of phenothiazines, carbazoles, and related diphenylamines were evaluated in the oxidation of tetralin at 60°C and linoleic acid micelles in aqueous dispersion at 37°C induced by an azo initiator. Phenothiazines were highly antioxidant in both systems. Although diphenylamine and carbazole were not good antioxidants, those having a hydroxy group as a substituent at the ortho or para position to the amino group were potently antioxidant. The antioxidant activity of o-hydroxydiphenylamine was much greater than that of other compounds in both systems due to a stabilization of the phenoxyl radical by delocalization of the unpaired electron to the p-type lone pair of the amino group. A semiempirical MNDO-AM1 calculation was applied to study hydrogen abstractions of antioxidants in the chain process of autoxidation. These results indicated that the rates of oxidation during the induction period correlated with the dissociation energies of the O-H or N-H bonds.
- Yamamura, Tatsuo,Suzuki, Kyouichi,Yamaguchi, Tatsuya,Nishiyama, Tomihiro
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p. 413 - 419
(2007/10/03)
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- ETHYLAMINO CARBAZOLE MELATONERGIC AGENTS
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Novel substituted carbazole compounds of Formula I are active as melatonergic agents: STR1 wherein: R 1 is C(O)R 3 or SO. sub. 2 R 4 ;R 2 is H or C 1-6 alkoxy;R 3 is C 1-6 alkyl, (CH 2) n SR 4, (CH. sub.2). sub.n OR 4, (CH 2) n SO 2 R 4, or NHR 4 ; R 4 is C 1-4 alkyl; andm is 1 or 2; andn is 1 to 4.
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- Chemoselective N-alkylation of 2-Hydroxycarbazole as a Model for the Synthesis of N-Substituted Pyrrole Derivatives Containing Acidic Functions
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2-Hydroxycarbazole (1) was chemoselectivity N-alkylated with several alkyl halides 3 by generating the corresponding N,O-dianion using excess sodium hydride in a suitable solvent, under anhydrous conditions.The highest yields, (87-96percent) of 9-alkyl-2-hydroxycarbazoles 4 and the mildest reaction conditions were reached in THF containing DMF as an additive (2 mol equiv), but other solvents (DMSO, diglyme, DME) or solvent-additive systems (THF-diglyme, THF-DMSO, DME-DMF, diglyme-DMF) are effective.
- Albanese, Domenico,Landini, Dario,Penso, Michele,Spano, Giovanni,Trebicka, Artan
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p. 5681 - 5688
(2007/10/02)
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- CARBAZOLE ALKALOIDS FROM GLYCOSMIS PENTAPHYLLA
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Three carbazole alkaloids, glycozolicine, 3-formyl carbazole and glycosinine, have been isolated from the roots of Glycosmis pentaphylla.The structures of glycozolicine and glycosinine have been established as 5-methoxy-3-methyl carbazole and 2-methoxy-3-formyl carbazole, respectively, from physical and chemical evidence, and synthesis. Key Word Index - Glycosmis pentaphylla; Rutaceae; roots; carbazole alkaloids.
- Jash, S. S.,Biswas, G. K.,Bhattacharyya, S. K.,Bhattacharyya, P.,Chakraborty, A.,Chowdhury, B. K.
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p. 2503 - 2506
(2007/10/02)
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- Oxidation of diphenylamines by iodate - A kinetic study
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Oxidation of diphenylamines (DPA) by iodate in aqueous methanol (70percent, v/v) at 303 K is first order in and fractional order in and is acid-catalysed.There is a dipole-dipole interaction between the oxidant and DPA.The substituent effect on the rate of reaction shows that electron-relasing groups on the benzene ring enhance the rate and electron-withdrawing groups retard the rate compared to the unsubstituted DPA.The product identified is the corresponding carbazole.Thermodynamic parameters are calculated and a suitable mechanism is proposed.
- Brahmaiah, A.,Manikyamba, P.,Sundaram, E.V.
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p. 247 - 251
(2007/10/02)
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