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Herein, we reveal a novel method for the synthesis of benzo[]carbazoles via palladium-catalyzed annulation between diarylalkynes and isocyanides. This method features excellent regioselectivity and chemoselectivity, mild reaction conditions, experimental simplicity, and good functional group tolerance. Further mechanistic investigations suggest that intramolecular 1,5-acyl migration is mainly involved in this reaction system. The feasibility of the strategy was further demonstrated by late-stage modifications and photophysical property studies.
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http://dx.doi.org/10.1021/acs.orglett.5c01463 | DOI Listing |
Org Lett
August 2025
Innovation Team of Optical Functional Molecular Devices, Inner Mongolia Key Laboratory for the Natural Products Chemistry and Functional Molecular Synthesis, College of Chemistry and Materials Science, Inner Mongolia Minzu University, Tongliao 028000, China.
A base-controlled rhodium(III)-catalyzed regioselective C-H alkylation and annulation of 2-arylindoles with α-Cl ketones in a single catalytic system is described, in which α-Cl ketones serve as C(sp)-based electrophilic partners and oxidized alkyne equivalents. When using NaOAc as the base, the C-H functionalization selectively delivered 1-aryl-2-(2-aryl-1-indol-3-yl)ethan-1-ones. In contrast, the same catalytic system with the base NaHCO predominately provided 5-aryl-11-benzo[]carbazoles.
View Article and Find Full Text PDFThorac Cancer
June 2025
Department of Biotechnology and Pharmaceutical Sciences, College of Pharmacy, Western University of Health Sciences, Pomona, California, USA.
Lung cancer is the most common and deadly type of cancer. Our previous study showed that carvedilol, a β-blocker, can prevent lung cancer induced by benzo(a)pyrene [B(a)P]. Carvedilol is a 1:1 racemic mixture of S- and R-carvedilol, with S-carvedilol acting as a β-adrenergic blocker, while R-carvedilol lacks β-blocking activity.
View Article and Find Full Text PDFChem Sci
July 2025
Faculty of Chemistry, University of Lodz 91-403 Lodz Poland
Photocyclization of N-substituted carbazole derivatives of benzo[][1,2,4]triazine gave two carbazole-fused Blatter radicals with a novel heterocyclic skeleton. No photocyclization was observed for the analogous dibenzocarbazole, indole, benzimidazole, and phenoxazine precursors, which was rationalized with DFT computational methods. The two carbazole-derived radicals were characterized by spectroscopic (UV-vis, EPR) and electrochemical methods, while one of them was analyzed structurally (XRD) and magnetically (SQUID).
View Article and Find Full Text PDFOrg Lett
June 2025
State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, P. R. China.
Herein, we reveal a novel method for the synthesis of benzo[]carbazoles via palladium-catalyzed annulation between diarylalkynes and isocyanides. This method features excellent regioselectivity and chemoselectivity, mild reaction conditions, experimental simplicity, and good functional group tolerance. Further mechanistic investigations suggest that intramolecular 1,5-acyl migration is mainly involved in this reaction system.
View Article and Find Full Text PDFRSC Adv
May 2025
Research Centre in Chemistry, Mahatma Gandhi Vidyamandir's Loknete Vyankatrao Hiray Arts, Science and Commerce College (Affiliated to Savitribai Phule Pune University, Pune) Panchavati Nashik Maharashtra 422003 India
In the search for novel antidepressant agents, twelve novel nitrogen-containing heterocycle-linked chalcone derivatives have been synthesized and comprehensively characterized using FT-IR, H NMR, C NMR, and Mass spectral methods. The synthetic strategy involves the preparation and optimization of reaction conditions for obtaining 4-carbazole-, indole-, and pyrrole-linked acetophenones, which were subsequently coupled with pyrazole aldehydes bearing piperidine, morpholine, benzotriazole, and imidazole ring systems. antidepressant activity of the compounds was evaluated using the Tail Suspension Test (TST) and Forced Swim Test (FST).
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