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Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines.
Org Biomol Chem
January 2025
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
1,4-Dibenzodiazepines, an important component of nitrogen-containing heterocycles, are widely present in drugs. Herein, we developed a photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions. A sequence of 11-alkyl-substituted 1,4-dibenzodiazepines were produced in 53%-85% yields, demonstrating excellent tolerance towards various functional groups.
View Article and Find Full Text PDFBF·EtO-promoted unconventional reactions of 2-oxoaldehyde: access to 4-amidooxazoles and β-keto amides/sulphonamides.
Org Biomol Chem
January 2025
Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu-180001, India.
This study investigates the potential of boron trifluoride etherate (BF·OEt) to trigger unprecedented reactions of 2-oxoaldehydes with nitriles and amides/sulphonamides. In contrast to the mechanism in conventional reactions, the α-carbonyl group in 2-oxoaldehydes induces a cyclization pathway to be followed when reacting with nitriles, yielding 4-amidooxazoles. Additionally, reactions with weak nucleophiles produce β-keto amides/sulphonamides.
View Article and Find Full Text PDFCopper-Catalyzed Radical Cascade Cyclization of -Substituted Indole-3-Aldehydes with Aryl Alkenes: Access to Pyrrolo[1,2-]indole Scaffolds.
J Org Chem
January 2025
Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan 250117, China.
Herein, we report a Cu-DTBP-catalyzed [3 + 2] cycloaddition reaction between 1-(2-oxo-2-phenylethyl)--indole-3-aldehyde and arylalkene, using DMF as the solvent. Under relatively mild reaction conditions, a series of indole compounds were synthesized in moderate yields (up to 73%). This protocol features good functional group tolerance and high atom economy.
View Article and Find Full Text PDFSilver-Catalyzed Cascade Radical Isonitrile Insertion/Defluorinative Cyclization: Direct Synthesis of 4-CFH-2-Phosphinoyl-quinolines.
J Org Chem
January 2025
Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China.
A novel silver-catalyzed cascade radical isonitrile insertion and defluorinative cyclization have been developed to synthesize CFH- and phosphinoyl-containing quinolines from -isocyanyl α-trifluoromethylstyrenes. The reaction proceeded under redox-neutral conditions and allowed the construction of a highly attractive quinoline ring system, with the simultaneous formation of the CFH group and introduction of various phosphinoyl groups in a single transformation, showing operational simplicity, a wide substrate scope, good tolerance for functional groups, and remarkable atom-/stepeconomy. Mechanistic studies indicated that the reaction is likely to involve the participation of P-centered radicals and key carbanion intermediates.
View Article and Find Full Text PDFVisible-Light-Driven Fluorescence Turn-on Photoswitches With Near Quantitative Photocyclization Yield.
Adv Sci (Weinh)
January 2025
School of Materials Science and Engineering, Zhengzhou University, No.100 Science Avenue, Zhengzhou, 450001, P. R. China.
Photoswitchable fluorescent materials have gained significant attention for their potential in advanced information encryption and anti-counterfeiting applications. However, the common use of UV light to trigger the isomerization processes leads to photobleaching and poor fatigue resistance. Visible-light-driven fluorescent photoswitches are highly desirable, but achieving high cyclization yield remains challenging.
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