3077-85-8Relevant articles and documents
A new method of nitration of carbazole and its derivatives
Pielichowski,Puszynski
, p. 772 - 774 (1974)
Carbazole and its derivatives were nitrated using cupric nitrate in the presence of acetic acid and acetic anhydride. Under these conditions, carbazole is nitrated to 3-nitrocarbazole, and N-alkylcarbazoles are nitrated to 3.6-dinitro derivatives.
Gas-Phase Reactivities and Interchromophoric Effects in 1,n-Dicarbazolylalkane Cations and Related Species
Schildcrout, Steven M.,Krafcik, Randolph B.,Masnovi, John
, p. 7026 - 7034 (1991)
The behavior of gaseous cations derived from electron ionization (20 and 70 eV) and methane chemical ionization (CI) of 1,n-dicarbazolylalkanes 1a-5a (where n = 1-5 methylene units, respectively) and the corresponding 3-nitro derivatives 1b-5b was examined using mass spectrometry.An iminium ion (m/z 180) is the major fragment from all 1-5 examined with the exception of 4a, for which CI affords predominantly a pyrrolidinium ion (m/z 222) by displacement of carbazole.Compounds 1a and 1b exhibit little *+ and + and undergo the most extensive fragmentation.Ethylated iminium ion (m/z 208) is observed from both 1a and 1b under CI conditions, indicating operation of an interannular hydrogen shift.Compound 3a fragments least, consistent with an exceptional, although small, stabilization for the parent ions of this derivative.
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.
Design, Synthesis and Discovery of N,N’-Carbazoyl-aryl-urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication
Spizzichino, Sharon,Mattedi, Giulio,Lauder, Kate,Valle, Coralie,Aouadi, Wahiba,Canard, Bruno,Decroly, Etienne,Kaptein, Suzanne J. F.,Neyts, Johan,Graham, Carl,Sule, Zakary,Barlow, David J.,Silvestri, Romano,Castagnolo, Daniele
supporting information, p. 385 - 390 (2020/01/24)
The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure-based virtual screening approach using the ZIKV NS5-MTase. A novel series of molecules with a carbazoyl-aryl-urea structure has been discovered and a library of analogues has been synthesized. The new compounds inhibit ZIKV MTase with IC50 between 23–48 μM. In addition, carbazoyl-aryl-ureas also proved to inhibit ZIKV replication activity at micromolar concentration.
Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 15793 - 15798 (2020/10/12)
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines
Akram, Manjur O.,Das, Avishek,Chakrabarty, Indradweep,Patil, Nitin T.
supporting information, p. 8101 - 8105 (2019/10/11)
The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0142-0146, (2019/07/18)
The present invention provides a compound of chemical formula 1 and an organic light emitting device comprising the same. The compound according to the present invention has excellent electrochemical and thermal stability, thereby having excellent lifespan characteristics.COPYRIGHT KIPO 2019
Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
Dalvi, Bhakti A.,Lokhande, Pradeep D.
supporting information, p. 2145 - 2149 (2018/05/08)
An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
Synthesis of Novel 3-N-substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation
Kim, Jiseon,Jung, Sang-Hyuk,Yun, Eunju,Cho, Soo-Hyun,Yuseok,Kim, Ji-Eun,Kim, Young-Ho,Myung, Chang-Seon,Song, Gyu-Yong
supporting information, p. 726 - 728 (2018/05/14)
The carbazole moiety exhibits various biological activities, including anticancer, antiviral, anti-inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3-N-substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with a urea linkage within the carbazole framework, exhibited the strongest inhibitory activity (98.25% at 30 μM). Interestingly, reduction of the nitro group of compound 5q to an amine exhibited significantly decreased activity (compound 5r, 5.18% at 30 μM). Also, substitution of the urea moiety of compound 5q with a carbamate moiety resulted in a considerable loss of activity (compound 8a, 5.91% at 30 μM). These results suggest that the urea moieties and nitro groups of 3-N-substituted carbazole derivatives may play key roles in inhibiting in vitro platelet aggregation induced by collagen.
Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D
Alimi, Isak,Remy, Richard,Bochet, Christian G.
, p. 3197 - 3210 (2017/06/21)
The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.
