Phosphine-Mediated [3+2] Cyclization for the Synthesis of Coumarin-Based CF3-Containing Furanones DOI

Wenhao Gan,

Junfeng Fu,

Yongjiang Wang

et al.

Synlett, Journal Year: 2023, Volume and Issue: 34(13), P. 1587 - 1592

Published: April 5, 2023

Abstract A tertiary phosphine-mediated [3+2] cyclization reaction of ynones with fluorinated coumarin derivatives has been developed to give a series coumarin-based CF3-containing furanones in moderate good yields under mild conditions. Preliminary investigation into their antitumor activities is also presented.

Language: Английский

Push–pull coumarin-based one-component iodonium photoinitiators for cationic nanocomposite 3D-VAT printing DOI Creative Commons
Filip Petko, Andrzej Świeży, Magdalena Jankowska

et al.

Polymer Chemistry, Journal Year: 2023, Volume and Issue: 14(25), P. 3018 - 3034

Published: Jan. 1, 2023

In this article, we described a new group of cationic photoinitiators.

Language: Английский

Citations

13
Photoredox-Catalyzed Redox-Neutral Decarboxylative C–H Acylations of Coumarins with α-Keto Acid DOI
Bin Sun, Yingying Wang, Jia‐Yin Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2466 - 2470

Published: March 31, 2023

A novel and green photocatalytic strategy for the synthesis of C-4-acylated coumarins with α-keto acids 3-nitrocoumarin has been developed. This operationally simple protocol works under mild reaction conditions, providing convenient access to 4-acyl coumarin derivatives. The control experimental results showed that nitro radical produced by cleavage C-N bond acts as an electron acceptor complete cycle, achieving a redox-neutral reaction.

Language: Английский

Citations

11
Pd(II)‐Catalyzed Selective [4+2] Benzannulations of Pyridones with Alkenes: Diversity‐Oriented Synthesis of a Novel Fluorescent Quinolinone DOI

Yiwei Xu,

Yuanyuan Wang,

Jing Li

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Comprehensive Summary Herein, an intermolecular palladium(II)‐catalyzed regioselective [4+2] benzannulation reaction capable of converting 2‐pyridones into quinolinones was developed using electron‐deficient alkenes as two‐carbon units. An examination the mechanism indicated that extension from 2‐pyridone to quinolinone likely facilitated through a series sequential C—H activation reactions or 6π electrocyclization, culminating in dehydrogenative aromatization. This method diversity‐oriented synthesis derivatives is characterized by broad substrate scope, atom economy, and excellent chemical selectivity. In addition, these exhibit fluorescent absorption within visible‐light spectrum, which makes them suitable candidates for development innovative probes.

Language: Английский

Citations

0
Visible‐Light‐Active Coumarin‐ and Quinolinone‐Based Photocatalysts and Their Applications in Chemical Transformations DOI
Myojeong Kim, Seonghyeok Hong, Jinwook Jeong

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(7)

Published: Jan. 10, 2023

Abstract Organic dyes have been actively studied as useful photocatalysts because they allow access to versatile structural flexibility and green synthetic applications. The identification of a new class robust organic chromophores is, therefore, in high demand increase diversity variability. Although coumarins quinolinones long acknowledged chromophores, their ability participate photoinduced transformations is somewhat less familiar. Fascinated by chromophoric features adaptable platform, our group interested the fluorescent bioactive molecules development methods using photocatalysts. This account provides an overview recent progress discovery application light‐absorbing coumarin quinolinone derivatives photochemistry medicinal chemistry.

Language: Английский

Citations

5
Diquat Based Dyes: A New Class of Photoredox Catalysts and Their Use in Aerobic Thiocyanation DOI Creative Commons

Armin Meier,

S. V. Badalov, Timur Biktagirov

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(22)

Published: Jan. 26, 2023

A series of new organic donor-π-acceptor dyes incorporating a diquat moiety as novel electron-acceptor unit have been synthesized and characterized. The analytical data were supported by DFT calculations. These explored in the aerobic thiocyanation indoles pyrroles. Here they showed high photocatalytic activity under visible light, giving isolated yields up to 97 %. In addition, standalone methyl viologen through formation an electron donor acceptor complex is presented.

Language: Английский

Citations

5
Intramolecular Palladium(II)-Catalyzed Regioselective 6-endo or 6-exo C–H Benzannulation: An Approach for the Diversity-Oriented Synthesis of Quinolinone Derivatives from Pyridones DOI

Ziyi Sun,

Fengya He,

Yiwei Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7058 - 7064

Published: April 29, 2024

Herein, a new intramolecular palladium(II)-catalyzed regioselective 6-

Language: Английский

Citations

1
Visible-light-induced tandem radical addition/cyclization of 2-alkenylphenols and CBr4 for the synthesis of 4-arylcoumarins DOI

Li-Ping Tan,

Dong Liang, Ying Cheng

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(18), P. 5052 - 5057

Published: Jan. 1, 2021

A visible-light-induced photoredox-catalyzed tandem radical addition/cyclization of 2-alkenylphenols and CBr 4 is developed, providing efficient practical access to various 4-arylcoumarins in a one-pot fashion.

Language: Английский

Citations

9
Photo‐Modulation of Gene‐Editing Enzymes CRISPR/Cas9 with Bifunctional Small‐Molecule Ligands† DOI Open Access
Yidan Zhang, Yixin Zhang,

Lili Han

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3639 - 3644

Published: Sept. 13, 2023

Comprehensive Summary The control of protein functions with light is valuable for spatiotemporal probing biological systems. Current small‐molecule photo‐ modulation methods include the light‐induced uncaging inhibitors and chromophore‐assisted inactivation reactive oxygen species (ROS). However, constant target expression results in inadequate photo‐modulation efficiency, particularly less potent chromophores. Herein, we report a novel bifunctional ligands strategy to photo‐modulate gene‐editing enzymes CRISPR/Cas9. A coumarin‐derived ligand Bhc‐BRD0539 developed uncage active inhibitor upon irradiation generate ROS Cas9 proximity dual inhibition activity. Our highlight synergistic ligands, which offers addition current CRISPR/Cas9 technologies may extend other classes.

Language: Английский

Citations

3
Solvent‐Dependent Photochemistry for Diverse and Selective C−H Functionalization of 2‐tert‐Butyl‐1,4‐Benzoquinones DOI

Cheol Hyeon Ka,

Da Seul Lee, Eun Jin Cho

et al.

ChemPhotoChem, Journal Year: 2022, Volume and Issue: 6(10)

Published: June 11, 2022

Abstract Controlling a reaction to selectively produce set of distinct valuable compounds from the same substrate is highly attractive topic in synthetic chemistry. In this work, solvent‐dependent photochemistry 2‐ tert ‐butyl‐1,4‐benzoquinones achieve diverse C−H functionalization was investigated, which afforded three selective transformations: (1) intermolecular C−O bond formation non‐fluorinated alcoholic solvents; (2) perfluorinated hexafluoroisopropanol solvent‐promoted intramolecular cyclization afford coumaran derivatives; (3) 1,4‐dioxane solvent‐induced hydrogen atom transfer 2‐methylallyl hydroquinones.

Language: Английский

Citations

5
Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update DOI Creative Commons
Aqsa Mushtaq, Muhammad Irfan, Atta ul Haq

et al.

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Dec. 13, 2024

2,3-Dihydrobenzofurans are noteworthy scaffolds in organic and medicinal chemistry, constituting the structural framework of many varied medicinally active compounds. Moreover, a diverse variety biologically potent natural products also contain this heterocyclic nucleus. Reflecting on wide biological substantiality dihydrobenzofurans, several innovative facile synthetic developments evolving to achieve these heterocycles. This review summarizes transition-metal-free, efficient, novel pathways toward constructing dihydrobenzofuran nucleus established after 2020.

Language: Английский

Citations

0