AI Article Synopsis
- Efficacious protocols have been developed to synthesize a unique coumarin-fused pyridone structure using cheap Ru(II) metal to activate specific carbon-hydrogen bonds.
- The process involves the use of a methoxy carboxamide as a tool for bond functionalization and includes diverse strategies for creating various heterocycles, including biologically relevant compounds like benzimidazole-fused coumarin.
- Additionally, the methodology shows promise for late-stage modifications and fluorescence quenching in response to aluminum ions, highlighting the versatility and potential advantages of the iodonium ylide-based approach.
Article Abstract
Efficacious protocols have been established to synthesize a structurally privileged Π-extended coumarin-fused pyridone nucleus by activating the vinylic C(sp)-H bond of coumarin-3-carboxamide under the influence of inexpensive Ru(II)-metal. Here an -methoxy carboxamide entity has been exploited as the chelating fragment to manifest C(sp)-H bond functionalization with a concomitant (4 + 2) annulation reaction, resulting in heterocyclic ring-forming protocols along with sulfoxonium ylide and iodonium ylide as representative bench-stable carbene surrogates. This diverse heterocycle formation carbene insertion strategies, is further expanded to activate the -C(sp)-H bonds of different heterocycles by employing the sp-N moiety as the directing group to develop acyl-alkylated/alkenylated quinazolines, isoxazoles and highly fluorescent pyridone--oxides. Intriguingly, during an evaluation of the versatility of the current protocols, a one-pot double C-H activation has been rationalized in the presence of iodonium ylide, which results in biologically potent benzimidazole-fused coumarin-centered bridge-headed polycyclic heteroarenes. Furthermore, a chemo-selective late-stage synthetic transformation is being designed to develop differently substituted pyridone analogues by switching the nature of the reducing agent. In addition, a photophysical experiment was done on one pyridine--oxide compound (7e) and delightfully it exhibited fluorescence quenching activity selectively in the presence of Al ions, which appears to be a unique feature of our methodology. Finally, upon correlation of the merit of the developed pathways, the iodonium ylide mediated strategy appears to be superior.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d3ob00828b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Palladium Iodide Catalyzed Multicomponent Carbonylative Synthesis of 2-(4-Acylfuran-2-yl)acetamides.
Molecules
September 2023
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende, Italy.
2-Propargyl-1,3-dicarbonyl compounds have been carbonylated under oxidative conditions and with the catalysis of the PdI/KI catalytic system to selectively afford previously unreported 2-(4-acylfuran-2-yl)acetamides in fair to good yields (54-81%) over 19 examples. The process takes place under relatively mild conditions and occurs via a mechanistic pathway involving C-H activation by oxidative monoamincarbonylation of the terminal triple bond of the substrates with formation of 2-ynamide intermediates, followed by 5---cyclization (via intramolecular conjugate addition of the in situ formed enolate to the 2-ynamide moiety) and aromative isomerization.
View Article and Find Full Text PDFRecent progress in the oxidative coupling of unactivated Csp-H bonds with other C-H bonds.
Chem Commun (Camb)
December 2021
Department of Chemistry, Fudan University, 2005 Songhu Rd, Shanghai, 200438, China.
Article Synopsis
- - The article discusses the oxidative coupling of carbon-hydrogen (C-H) bonds as a simple and efficient way to create carbon-carbon (C-C) bonds from hydrocarbons without needing any prior modifications.
- - It highlights recent advancements in coupling unactivated Csp-H bonds with various hybrid C-H bonds, including combinations with Csp-H bonds.
- - The paper provides a summary of the types of substrates used, proposed reaction mechanisms, and potential applications, aiming to inspire new methods for building Csp-C bonds effectively.
Metal-Catalyzed Decarboxylative C-H Functionalization.
Chem Rev
July 2017
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences , Fuzhou, Fujian 350002, China.
Article Synopsis
- C-H bond activation and decarboxylation are important techniques in organic synthesis, leading to a new method called decarboxylative C-H bond functionalization.! -
- This review highlights recent advancements in utilizing this method to synthesize various organic compounds, including styrenes, chalcones, and heterocycles.! -
- The article discusses the effectiveness, limitations, and potential applications of decarboxylative functionalization across different types of C-H bonds.!
Synthesis of bicyclic p-diiodobenzenes via silver-catalyzed Csp-H iodination and ruthenium-catalyzed cycloaddition.
J Am Chem Soc
June 2006
Department of Applied Chemistry Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.
Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2 + 2 + 2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.
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!