Functionalized Quinolones and Isoquinolones via 1,2-Difuntionalization of Arynes: Synthesis of Antagonist Agent AS2717638 and Floxacin Key Intermediates DOI

Sachin D. Mahale,

Anamika Prasad,

Santosh B. Mhaske

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Demonstrated herein is a switchable approach for selective synthesis of quinolones and isoquinolones via 1,2-difunctionalization arynes its application in the antagonist agent AS2717638 floxacin key intermediates.

Language: Английский

Triazine-Modified Color-Responsive Triarylboron/Acridine Fluorescent Probe with Multi-Channel Charge Transfer for Highly Sensitive Fluoride Ion Detection DOI Creative Commons
Lei Tang,

Jiaoyun Wang,

Yuan Liu

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(4), P. 879 - 879

Published: Feb. 14, 2025

A novel fluoride ion fluorescent probe is designed by introducing the strong electron-withdrawing triazine groups into triarylboron/acridine conjugation system. The A-D-A' molecular configuration endows this molecule with multiple charge-transfer channels; upon reaction F-, act as primary acceptors within molecule, facilitating charge transfer between acridine units and groups. During detection, changes in triarylboron moiety lead to a significant bathochromic-shift fluorescence emission from green yellow. Theoretical calculations attribute phenomenon reduction S1 state energy level fluorination, resulting pronounced visible color change chromogenic response during detection. Based on intensity varying degrees of F- coordination, detection limit low 10-7 M was determined for TB-1DMAc-2TRZ, demonstrating high sensitivity probe.

Language: Английский

Citations

1
Construction of Asymmetric C–S Bonds via an Electrochemical Catalysis DOI
Xiang Sun, Yan Zhang,

Tong Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1566 - 1572

Published: Feb. 16, 2024

Construction of asymmetric C–S bonds was realized via electrochemical catalysis in the presence a chiral nickel complex. The reaction can be carried out with excellent stereoselectivity and great functional group tolerance. corresponding products provide crucial precursors for some materials pharmaceutical drugs.

Language: Английский

Citations

8
Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes DOI
Nayoung Kim,

Myungsoo Choi,

Sung‐Eun Suh

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(20), P. 11435 - 11522

Published: Oct. 9, 2024

Arynes hold significance for the efficient fusion of (hetero) arenes with diverse substrates, advancing construction complex molecular frameworks. Employing multiple equivalents arynes is particularly effective in rapid formation polycyclic cores found optoelectronic materials and bioactive compounds. However, inherent reactivity often leads to side reactions, yielding unanticipated products underlining importance a detailed investigation into use fine-tune their reactivity. This review centers on methodologies syntheses organic reactions involving arynes, categorizing based mechanisms like cycloadditions, σ-bond insertions, nucleophilic additions, ene discusses aryne polymerization. The categorization these includes two primary approaches: first entails engagement within single step while second approach involves using equivalent sequentially across steps, both requiring strict control ensure precise participation each respective step. Additionally, provides an in-depth analysis selection precursors, organized chronologically by activation strategy, offering comprehensive background that supports main theme utilization. expectation remains this will be invaluable designing advanced engaging arynes.

Language: Английский

Citations

7
Selective S-Arylation of Sulfenamides with Arynes: Access to Sulfilimines DOI

Yifeng Guo,

Zhe Zhuang, Xiaoying Feng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7192 - 7197

Published: Sept. 21, 2023

Sulfilimines, the aza analogues of sulfoxides, are increasing interest in medicinal and agrochemical research programs. However, development efficient routes for their synthesis has remained relatively unexplored. In this study, we report a transition metal-free, selective S-arylation reaction between sulfenamides arynes, enabling facile preparation structurally diverse sulfilimines under mild redox-neutral conditions good yields. The application value our method was further demonstrated by scale-up synthesis, downstream derivatization, robustness screen.

Language: Английский

Citations

15
Ring Expansion of Cyclic Boronates via Oxyboration of Arynes DOI
Y. Shiratori, Julong Jiang, Koji Kubota

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(3), P. 1765 - 1770

Published: Jan. 10, 2024

The oxyboration of arynes was achieved for the first time. A series 2-aryl-1,3,2-dioxaborolane derivatives were reacted with aryne precursors in presence CsF to give corresponding ring-expanded seven-membered borinic acid esters via selective boron–oxygen bond activation. Preliminary experimental mechanistic studies and density functional theory (DFT) calculations suggest that this unprecedented proceeds through formation boron ate complexes arylboronates CsF, followed by insertion into bond.

Language: Английский

Citations

5
Synthesis of novel skipped diene-3-halocoumarin conjugates as potent anticancer and antibacterial biocompatible agents DOI Creative Commons
Yasser Fakri Mustafa,

Duha Adnan Hassan,

Ayman Faris Faisal

et al.

Results in Chemistry, Journal Year: 2024, Volume and Issue: 11, P. 101846 - 101846

Published: Oct. 1, 2024

Language: Английский

Citations

5
Bromothiolation of Arynes for the Synthesis of 2-Bromobenzenethiol Equivalents DOI Creative Commons

Shinya Tabata,

Suguru Yoshida

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3816 - 3821

Published: April 30, 2024

A new method to synthesize o-bromobenzenethiol equivalents through aryne intermediates is disclosed. Various are prepared by the bromothiolation of with potassium xanthates. Aryl xanthates serve in synthesis diverse organosulfurs involving phenothiazines and thianthrenes further transformations.

Language: Английский

Citations

4
Copper-Mediated Deconstructive Ring Cleavage of Cyclic Thioethers with Boron Compounds DOI
Guanyu Wang,

Dongchang Han,

Yue Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3522 - 3526

Published: May 9, 2023

The deconstructive ring cleavage of cyclic thioethers is achieved through a Chan–Lam type process with boron compounds. sequential hydroboration/ring from alkynes offered new route to the preparation vinyl sulfides based on developed conditions. Further exploration has demonstrated versatility nucleophiles, delivering various functionalized featuring linear frameworks.

Language: Английский

Citations

10
Precise synthesis of ortho-deuterated aromatic derivatives: an arylthianthrenium salt-based platform approach DOI

Yunhao Guan,

Peng Xia, Rong Fan

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111132 - 111132

Published: March 1, 2025

Language: Английский

Citations

0
Exploration of the Chan–Lam Reaction for an Undergraduate Organic Chemistry Laboratory Course DOI
Zhibin Luo, Bin Liu

Journal of Chemical Education, Journal Year: 2025, Volume and Issue: unknown

Published: May 12, 2025

Language: Английский

Citations

0