Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of -acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6384560 | PMC |
| http://dx.doi.org/10.3390/molecules24030459 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of 2-Acyltryptamines through an Unexpected Brønsted Acid Catalyzed Formal 1,5-Migration of Functional Group from Indole-Tethered Ynamides.
J Org Chem
September 2025
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi),
Herein, we have developed a Brønsted acid catalyzed 1,5-migration of functional groups from indole-tethered ynamides to prepare a variety of 2-acyltryptamines in good to excellent yields with high site-selectivity at the C2-position of indoles. Mechanistic studies revealed that the reaction underwent an intramolecular cyclization, 1,2-migration of the vinyl group, and C-N bond cleavage by hydrolysis in a one pot. The reaction features broad substrate scope, good functional group compatibility, 1,5-migration of functional groups, C-N bond cleavage to form C-C bond, and diverse 2-acyltryptamine scaffolds.
View Article and Find Full Text PDFUnique halogen-π association detected in single crystals of C-N atropisomeric -(2-halophenyl)quinolin-2-one derivatives and the thione analogue.
Beilstein J Org Chem
September 2025
Chemistry and Materials Program, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
In single crystals of C-N atropisomeric -(2-halophenyl)quinolin-2-one and the thione analogue, a unique association based on a halogen-π interaction was detected. In racemic and optically pure -(2-bromo- or 2-chlorophenyl)quinolin-2-ones, homochiral layered polymers, which consist of ()- or ()-atropisomers, were formed through intermolecular halogen-π association. The halogen-π association in the racemates is due to a halogen bond (C-X···π) between a σ-hole on the halogen atom and a π-electron on the quinolinone benzene ring, while that in optically pure forms is caused by an n-π* interaction between a lone electron pair on the halogen atom and a π* orbital of the quinolinone.
View Article and Find Full Text PDFUnveiling the binding details of berberine mid-chain fatty acid salts on lysozyme: Multi-spectroscopy and molecular docking.
Spectrochim Acta A Mol Biomol Spectrosc
September 2025
College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, PR China.
The interactions of three berberine mid-chain fatty acid salts ([BBR][C], n = 6, 7, 8) with lysozyme (Lyz) are investigated in detail using multi-spectroscopic and molecular docking techniques. Steady-state fluorescence and UV-visible absorption experiments suggest that the binding mechanism of [BBR][C] on Lyz is a static quenching with a binding ratio of 1:1. The compound [BBR][C] exhibits a moderate binding affinity toward Lyz.
View Article and Find Full Text PDFAll Roads Lead to Carbinolamine: QM/MM Study of Enzymatic C-N Bond Cleavage in Anaerobic Glycyl Radical Enzyme Choline Trimethylamine-Lyase (CutC).
J Phys Chem B
September 2025
Centre for Computational Chemistry, School of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
The anaerobic glycyl radical enzyme choline trimethylamine-lyase (CutC) is produced by multiple bacterial species in the human gut microbiome and catalyzes the conversion of choline to trimethylamine (TMA) and acetaldehyde. CutC has emerged as a promising therapeutic target due to its role in producing TMA, which is subsequently oxidized in the liver to form trimethylamine--oxide (TMAO). Elevated TMAO levels are associated with several human diseases, including atherosclerosis and other cardiovascular disorders─a leading cause of mortality worldwide.
View Article and Find Full Text PDFElectrochemical Oxidative Ring Opening of 1-Acetylindoline-3-one to Access α-Ketoamides.
J Org Chem
September 2025
Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781039, India.
The synthesis of α-ketoamides through oxidative ring opening of 1-acetylindoline-3-one under electrochemical conditions is reported. In an undivided cell, the reaction proceeds via the formation of an iminium ion intermediate, nucleophilic attack by a hydroxide ion, and subsequent ring opening through pre-existing C-N bond cleavage. The reaction in the presence of HO confirms that the amidic oxygen originated from the moisture present in the medium.
View Article and Find Full Text PDF