239-01-0Relevant articles and documents
Efficient synthesis of 1,2,3,4-tetrahydro-11H-benzo[a]carbazole and its regioselective oxidation
Dufour, Fabien,Kirsch, Gilbert
, p. 1021 - 1022 (2006)
Carbazole derivative 4 was synthesized in an efficient three-step sequence and its further oxidation with dichlorodicyanoquinone gave selectively 4-oxo-1,2,3,4-tetrahydro-11H-benzo[a]carbazole 3. Georg Thieme Verlag Stuttgart.
A one-pot direct regioselective iodination of Fischer-Borsche product using periodic acid in PEG-400
Ghom, Monica H.,Naykode, Mahavir S.,Humne, Vivek T.,Lokhande, Pradeep D.
, p. 1029 - 1031 (2019)
A metal-free and greener approach for the one-pot direct iodination and dehydrogenation of dihydrobenzo[a]carbazoles has been developed using periodic acid in polyethylene glycol-400 (PEG-400) under mild condition. This method has been proven to be tolerate to a broad range of functional groups, with good to excellent yields include metal-free inexpensive catalyst, easy work-up, benign reaction condition and high regioselectivity. The solvent has been successfully recycled up to 5 times without any loss of activity in an aqueous medium.
Behavior of oxotetrahydrobenzo[b]- and [c]thiophenes and their α-hydroxymethylene derivatives in the fischer indole synthesis
Martarello, Laurent,Joseph, Delphine,Kirsch, Gilbert
, p. 367 - 379 (1996)
We described an approach to thienocarbazoles via a Fischer indole synthesis starting directly from oxotetrahydrobenzo[b]- and [c]thiophenes or from their α-hydroxymethylene derivatives with a Japp-Klingemann reaction to make the hydrazones which are cyclised under acidic conditions.
Chemoselective Borono-Catellani Arylation for Unsymmetrical Biaryls Synthesis
Wang, Peng,Chen, Shuqing,Zhou, Zhiyu,Cheng, Hong-Gang,Zhou, Qianghui
, p. 3323 - 3327 (2019)
Reported is the borono-Catellani arylation process for unsymmetrical biaryls synthesis, utilizing the readily available pinacol ester of arylboronic acids, aryl bromides, and olefins as the reactants. The distinct reactivity of arylboronic ester and aryl bromides secures the excellent chemoselectivity in the pivotal arylation step. The reaction is enabled by the cooperative catalysis of Pd(OAc)2 and the NBE derivative N7, with molecular oxygen as the terminal oxidant.
Novel D-π-A benzocarbazole dyes with simple structures for efficient dye-sensitized solar cells
Han, Liang,Meng, Xiaozhou,Ke, Yong'an,Ye, Hongqiang,Cui, Yanhong
, p. 127 - 134 (2019)
Three benzocarbazole dyes were synthesized with N-butylbenzocarbazole as the electron donor, benzene, furan and thiophene as π-bridge, and cyanoacrylic acid as the electron acceptor. Their photophysical properties and photovoltaic performance were investigated and compared among three π-bridges. The incorporation of thiophene or furan unit favors intramolecular charge transfer through reducing the energy gap and improving the molecular conjugation due to their electron-rich properties and small volume compared with benzene unit. On the other hand, weakening coplanarity of dye with benzene bridge contributes to the antiaggregation and accordingly increase VOC, though decreases photo-generated current. Among three dyes, dye with furan bridge achieves the optimal photovoltaic performance 7.67% due to the highest JSC 15.45 mA cm?2.
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
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.
NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 5349 - 5353 (2021/07/21)
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.
COMPOSITION, ORGANIC OPTOELECTRONIC DEVICE, AND DISPLAY DEVICE
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Paragraph 0163; 0166-0167; 0183; 0186-0187, (2021/03/13)
A composition including a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and a second compound represented by Chemical Formula 3, an organic optoelectronic device, and a display device are related. In Chemical Formula 1 to Chemical Formula 3, each substituent is the same as described in the specification.
Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst
Steingruber, H. Sebastián,Mendioroz, Pamela,Volpe, María A.,Gerbino, Darío C.
, p. 4048 - 4058 (2021/08/03)
An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.
Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source
Guan, Xinyu,Zhu, Haoran,Zhao, Yingwei,Driver, Tom G.
supporting information, p. 57 - 60 (2019/12/11)
A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.
