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A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (S(E)Ar) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.
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http://dx.doi.org/10.1021/ol400371h | DOI Listing |
J Phys Chem A
September 2025
MOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, Guangdong Provincial Key Laboratory of Laser Life Science, Guangzhou Key Laboratory of Spectral Analysis and Functional Probes, College of Biophotonics, School of Optoelectronic Science and Engineering, South China Normal Un
In this study, we tackle the challenge of synthesizing nitrogen-containing bicyclic compounds in the gas phase, a topic of considerable interest to interstellar chemistry and combustion science. We specifically explore the bimolecular reaction between the -pyridinyl radical (CHN•), a quintessential nitrogen-containing monocyclic carbon-centered aromatic radical, and the interstellar molecule acrylonitrile (CHN) in a resistance-heated silicon carbide (SiC) microreactor. Utilizing advanced molecular beam-sampled synchrotron VUV photoionization mass spectrometry (SVUV-PIMS), we detected the formation of CHN species at 1100 K.
View Article and Find Full Text PDFJ Org Chem
September 2025
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, P. R. China.
A visible-light-induced dehydrogenative cyclization of -aryl benzaldehydes has been developed by using bench-stable -aminopyridinium salt as both a HAT reagent and a mild oxidant, which affords a wide range of fluorenones with diverse substitution patterns in moderate to excellent yields. Furthermore, this protocol is applicable to the synthesis of the natural product Nobilone. Mechanism investigation supports a photoinduced homocleavage of -aminopyridinium salt and a radical chain process.
View Article and Find Full Text PDFProc Natl Acad Sci U S A
August 2025
Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
Berberine bridge enzyme (BBE)-like enzymes catalyze various oxidative cyclization and dehydrogenation reactions in natural product biosynthesis, but the molecular mechanism underlying the selectivity remains unknown. Here, we elucidated the catalytic mechanism of BBE-like oxidases from involved in the oxidative cyclization and dehydrogenation of moracin C. X-ray crystal structures of a functionally promiscuous flavin adenine dinucleotide (FAD)-bound oxidase, MaDS1, with and without an oxidative dehydrogenation product were determined at 2.
View Article and Find Full Text PDFAnal Chem
August 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P.R. China.
Elucidating reaction mechanisms in heterogeneous catalysis demands real-time tracking of transient species at the solid-liquid interface. To address limitations in directly probing surface processes with conventional mass spectrometry (MS), this work develops an innovative "in-source reaction" strategy by integrating the reactor with the electrospray ionization (ESI) source. Diverse catalysts (e.
View Article and Find Full Text PDFChem Sci
August 2025
Key Laboratory of Pollution Processes and Environmental Criteria (Ministry of Education)/Tianjin Key Laboratory of Environmental Remediation and Pollution Control, Carbon Neutrality Interdisciplinary Science Center, College of Environmental Science and Engineering, Nankai University Tianjin 300350 C
The development of hydrogen- and solvent-free catalytic systems for plastic valorization requires precise control over metal speciation to enhance both catalytic efficiency and selectivity. Ru atomic clusters (ACs) on HZSM-5 zeolite show a turnover frequency of 52.71 mg mg h in low-density polyethylene (LDPE) conversion, a fivefold increase compared to traditional nanoparticles (NPs) at 10.
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