A Lewis acid-catalyzed electrophilic dearomatizative thiocyanation and cyclization of benzofurans with -thiocyanatosuccinimide has been accomplished by Lewis acid catalysis with CuOTf under mild conditions. It was suggested that the electrophilic thiocyanating reagent was activated by CuOTf, and difunctionalization was achieved through a thiocyanation/spirocyclization pathway. Thus, a series of thiocyanato-containing spiroketals were obtained in moderate to high yields. It provides an alternative approach for the synthesis of functionalized [6,5]/[5,5]-spiroketals.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d3ob00438d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Solid/Gas Reactivity of an Ir(I) Methylidene Complex.
Organometallics
December 2024
Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
stabilization of known, but solution unstable, methylidene complex [Ir(Bu-PONOP)(=CH)][BAr ] allows single-crystal to single-crystal solid/gas reactivity associated with the {Ir=CH} group to be studied. Addition of H results in [Ir(Bu-PONOP)(H)][BAr ]; exposure to CO forms iridium(I) carbonyl [Ir(Bu-PONOP)(CO)][BAr ], and reaction with NH gas results in the formation of methylamine complex [(Bu-PONOP)Ir(NHMe)][BAr ] via an aminocarbene intermediate. Periodic density functional theory and electronic structure analyses confirm the Ir=CH bond character but with a very low barrier to rotation around the Ir=CH bond.
View Article and Find Full Text PDFExcited-state antioxidant activity for apigenin based on external electric field-modulated ESIPT behavior: TD-DFT and molecular docking calculations.
J Photochem Photobiol B
December 2024
College of Science, Northeast Forestry University, Harbin 150040, China. Electronic address:
Apigenin (Api), a flavonoid possessing dual features of antioxidant activity and intramolecular hydrogen bond (IMHB), is subjected to an external electric field (EEF) to investigate its excited-state antioxidant activity after excited state intramolecular proton transfer (ESIPT) behavior employing the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods, as well as molecular docking. The existence of IMHB is demonstrated by structural parameters and AIM topological analysis, where Api in the enol form under an EEF of +60 × 10 a.u.
View Article and Find Full Text PDFGenotoxic effects of NDMA-contaminated ranitidine on Allium cepa cells and unveiling carcinogenic mechanisms via DFT and molecular dynamics simulation study.
Sci Rep
December 2024
Department of Genetic Engineering and Biotechnology, University of Rajshahi, Rajshahi, 6205, Bangladesh.
This study investigated the potential genotoxic and carcinogenic effects of N-nitrosodimethylamine (NDMA), a hazardous compound found in ranitidine formulations that are used to treat excessive stomach acid. The study first examined the effects of NDMA-contaminated ranitidine formulation on Allium cepa root growth and mitotic activity. The results demonstrated dose-dependent decreases in both root growth and mitotic index indicating genotoxicity and cell division disruption.
View Article and Find Full Text PDFChemoselective Stabilized Triphenylphosphonium Probes for Capturing Reactive Carbonyl Species and Regenerating Covalent Inhibitors with Acrylamide Warheads in Cellulo.
J Am Chem Soc
December 2024
Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, Taipei 106319, Taiwan (R.O.C.).
Reactive carbonyl species (RCS) are important biomarkers of oxidative stress-related diseases because of their highly reactive electrophilic nature. Despite their potential as triggers for prodrug activation, selective labeling approaches for RCS remain limited. Here, we utilized triphenylphosphonium groups to chemoselectively capture RCS via an aqueous Wittig reaction, forming α,β-unsaturated carbonyls that enable further functionalization.
View Article and Find Full Text PDFPhotoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with -Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins.
J Org Chem
December 2024
Henan Key Laboratory of Nanocomposites and Applications; Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, China.
A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using -aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct a wide range of 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that the reaction proceeds via a distinctive -aminopyridinium salt-promoted electrophilic amination of 2-styrylbenzoic acids.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!