A visible-light-accelerated Rh(III)-catalyzed C-H annulation of aromatic amines with bicyclic alkenes for the synthesis of benzocarbazole derivatives was developed. In this approach, with the cooperation of rhodium catalysis and visible-light irradiation, various aromatic amines reacted with oxabicyclic alkenes and azabicyclic alkenes smoothly at room temperature, delivering the corresponding bridged oxa or aza tetrahydro benzocarbazoles in good to excellent yields. Moreover, a series of benzo[]carbazoles were synthesized conveniently through further aromatization in one pot. The potential of this method was demonstrated via directing-group removal, derivatization, a scale-up reaction, and fluorescence investigations.
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http://dx.doi.org/10.1021/acs.orglett.1c02709 | DOI Listing |
Toxics
January 2025
Masonic Cancer Center, Division of Pediatric Epidemiology and Clinical Research, University of Minnesota, Minneapolis, MN 55455, USA.
Heterocyclic aromatic amines (HAAs), formed during the cooking of meat, are potential human carcinogens, underscoring the need for long-lived biomarkers to assess exposure and cancer risk. Frequent consumption of well-done meats containing 2-amino-1-methyl-6-phenylimidazo[4,5-]pyridine (PhIP), a prevalent HAA that is a prostatic carcinogen in rodents and DNA-damaging agent in human prostate cells, has been linked to aggressive prostate cancer (PC) pathology. African American (AA) men face nearly twice the risk for developing and dying from PC compared to White men.
View Article and Find Full Text PDFAnal Chem
January 2025
Xinjiang Key Laboratory of Trace Chemical Substances Sensing, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830000, China.
The specific fluorescent detection of α-methyltryptamine (AMT) presents a great challenge because similar amine groups and benzene rings exist in a variety of amines. Here, we show the precise modulation of the electron-withdrawing strength of the π-conjugate bridge in aldehyde-containing Schiff base-based fluorescent probes for ultratrace AMT discrimination. It is found that different electron-withdrawing groups -CH, -CHN, and -CHBr as the π-conjugate bridge of the 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF)-based probes can classify and identify organic amines with different amine nucleophilicities.
View Article and Find Full Text PDFChem Sci
January 2025
School of Chemistry and Chemical Engineering, Shandong University Jinan 250100 PR China
Noncovalent forces have a significant impact on photophysical properties, and the flexible employment of weak forces facilitates the design of novel luminescent materials with a variety of applications. The arene-perfluoroarene (AP) force, as one type of π-hole/π interaction, shows unique directionality, involving an electron-deficient π-hole interacting with a π-electron-rich region, facilitating precise orientation and stabilization in supramolecular structures. Here we present an amination engineering protocol to build a perfluoroarene library based on an octafluoronaphthalene skeleton with various steric and electronic properties.
View Article and Find Full Text PDFSci Rep
January 2025
Department of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran.
Herein, a novel amine-functionalized magnetic resorcinol-formaldehyde with a core-shell structure (FeO@RF/Pr-NH) is prepared through the chemical immobilization of (3-aminopropyl)trimethoxysilane over FeO@RF composite. Characterization through FT-IR, EDX, PXRD, and TGA confirmed successful surface modification while preserving the crystalline structure of FeO. The VSM analysis demonstrated excellent superparamagnetic properties, and SEM and TEM images revealed spherical particles for the designed nanocatalyst.
View Article and Find Full Text PDFJ Environ Manage
January 2025
College of Environment, Hohai University, Nanjing, 210098, PR China; Suzhou Research Institute, Hohai University, Suzhou, 215100, PR China; Ministry of Education Key Laboratory of Integrated Regulation and Resource Development on Shallow Lakes, Hohai University, Nanjing, 210098, PR China. Electronic address:
The ozone micro-bubbles (OCBs) technology is increasingly gaining traction as a promising alternative method for organic compounds removal in wastewater. Nevertheless, there is a scarcity of literature addressing the molecular-level transformation of organic compounds during OCBs treatment. In this work, the secondary effluent from a wastewater treatment plant was treated with ozone milli-bubbles (OLBs) and OCBs, and the fate of organic compounds at the molecular level was investigated using comprehensive two-dimensional gas chromatography quadrupole time-of-flight mass spectrometry (GC × GC-QTOF-MS).
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