Synthesis of Nitroso, Nitro, and Related Compounds DOI
Tom G. Driver, Van V. Vu

Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown

Published: Jan. 1, 2023

Language: Английский

Bio-Inspired Consecutive Photocatalyzed C–H Nitration of Arenes DOI

Da-Lie An,

Chao Xu, Manman Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

Concerned with traditional nitration methods requiring high temperatures, strong acids, or oxidizing agents, we developed an acid-free, selective photocatalytic method using riboflavin tetraacetate and Fe(NO3)3·9H2O under visible light. This efficiently nitrates various arenes bioactive molecules selectivity functional group tolerance, offering a sustainable alternative to techniques.

Language: Английский

Citations

0
Site-Selective Nitration of Arene via Hypervalent Iodine-Mediated C–H Functionalization DOI
Ziyang Zhang,

Wenjing Bao,

Guangxing Gu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 7, 2025

We developed a novel nitration method using hypervalent iodine for site-selective C-H functionalization. This technique efficiently synthesizes nitroarenes with high regioselectivity and is scalable, enhancing the late-stage modification of bioactive pharmaceuticals.

Language: Английский

Citations

0
Trifluoromethanesulfonic Acid Promoted Controllable Electrophilic Aromatic Nitration DOI

Yanxuan Wu,

Wen Lu, Yan‐Na Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11322 - 11327

Published: July 18, 2023

In this work, we developed a facile and controllable electrophilic aromatic nitration method with commercially available 68% HNO3 as the nitrating reagent trifluoromethanesulfonic acid (HOTf) catalyst in hexafluoroisopropanol or under solvent-free conditions. The products of different arenes can be obtained almost quantitative yields by tuning loading HOTf. strong acidity water absorbing property HOTf allowed transformation to reach completion short time at room temperature.

Language: Английский

Citations

8
Naphthyl-Substituted Indole and Pyrrole Carboxylic Acids as Effective Antibiotic Potentiators—Inhibitors of Bacterial Cystathionine γ-Lyase DOI Open Access
Andrey Kuzovlev, Mikhail D. Zybalov, Andrey V. Golovin

et al.

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(22), P. 16331 - 16331

Published: Nov. 15, 2023

Over the past decades, problem of bacterial resistance to most antibiotics has become a serious threat patients' survival. Nevertheless, novel class have not been approved since 1980s. The development antibiotic potentiators is an appealing alternative challenging process searching for new antimicrobials. Production H2S-one leading defense mechanisms crucial survival-can be influenced by inhibition relevant enzymes: cystathionine γ-lyase (bCSE), β-synthase (bCBS), or 3-mercaptopyruvate sulfurtransferase (MST). first one makes main contribution H2S generation. Herein, we present data on synthesis, in silico analyses, and enzymatic microbiological assays bCSE inhibitors. Combined molecular docking dynamics analyses revealed binding mode these ligands bCSE. Lead compound 2a manifested strong potentiating activity when applied combination with some commonly used against multidrug-resistant Acinetobacter baumannii, Pseudomonas aeruginosa, methicillin-resistant Staphylococcus aureus. was found favorable vitro absorption, distribution, metabolism, excretion, toxicity parameters. high effectiveness safety it promising candidate enhancing high-priority pathogens.

Language: Английский

Citations

8
DNDMH-mediated direct nitration of aryl alkenes DOI

Lihua Niu,

Hao Guo,

F. Y. Jia

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(23), P. 3202 - 3204

Published: Jan. 1, 2024

Direct nitration of aryl alkenes is enabled by DNDMH, a mild tool developed previously in our laboratory. It exhibits new property DNDMH through probably the delivery nitro radical with aid TEMPO and Cu(OAc) 2 .

Language: Английский

Citations

2
Nitration of Derivatives of Imidazo[1,5‐a]pyridine via C−H Functionalization with Fe(NO3)3 ⋅ 9H2O as a Promoter and a Nitro Source DOI
Xiaohan Yang,

Bi‐Qin Wang,

Qian Zhang

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(23)

Published: June 18, 2024

Abstract An additive‐free, mild, and regioselective C(1)−H nitration of imidazo[1,5‐a]pyridine derivatives was developed. This protocol features the use easily handled, commercially available, nontoxic Fe(NO 3 ) ⋅ 9H 2 O both as a source promoter, exhibits good functional group compatibility, generates desired nitrated products in acceptable to excellent yields. Mechanistic studies proposed that reaction may involve radical C−H functionalization process.

Language: Английский

Citations

2
Photochemical Nitration of Protected Anilines by 5‐Methyl‐1,4‐dinitroimidazole DOI

Xinlong Fan,

Yue Zhao, Lei Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(13), P. 1589 - 1593

Published: Jan. 30, 2023

Comprehensive Summary Nitroanilines are important building blocks in pharmaceuticals, materials and dyes. Nitration methods for anilines under mild conditions highly desired. Herein, we report a photochemical method the nitration of bearing various protecting groups by 5‐methyl‐1,4‐dinitroimidazole as new type nitro source. This is light‐controlled proceeds reaction with high efficiency. Fmoc‐, Ts‐ alkyl‐protected all well nitrated good functional group tolerance.

Language: Английский

Citations

4
The first example of a cine-substitution in a series of 1,3-dinitropyrazoles DOI
Tatyana K. Shkineva,

Svetlana A. Krasnova,

Igor L. Dalinger

et al.

Chemistry of Heterocyclic Compounds, Journal Year: 2024, Volume and Issue: 60(5-6), P. 257 - 261

Published: June 1, 2024

Language: Английский

Citations

1
Regioselective C(sp2)-H Nitrosation and Nitration of (Hetero)arenes with Fe(NO3)3·9H2O as Promoter, Nitroso and Nitro Source DOI
Ailong Shao, Yuanyuan Li, Min Dong

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134329 - 134329

Published: Oct. 1, 2024

Language: Английский

Citations

1
Catalytic ipso‐Nitration of Organosilanes Enabled by Electrophilic N‐Nitrosaccharin Reagent DOI Creative Commons
Ivan Mosiagin, Anthony J. Fernandes, Alena Budinská

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(41)

Published: Aug. 26, 2023

Abstract Nitroaromatic compounds represent one of the essential classes molecules that are widely used as feedstock for synthesis intermediates, preparation nitro‐derived pharmaceuticals, agrochemicals, and materials on both laboratory industrial scales. We herein disclose efficient, mild, catalytic ipso ‐nitration organotrimethylsilanes, enabled by an electrophilic N ‐nitrosaccharin reagent allows chemoselective nitration under mild reaction conditions, while exhibiting remarkable substrate generality functional group compatibility. Additionally, conditions proved to be orthogonal other common functionalities, allowing programming molecular complexity via successive transformations or late‐stage nitration. Detailed mechanistic investigation experimental computational approaches strongly supported a classical aromatic substitution (S E Ar) mechanism, which was found proceed through highly ordered transition state.

Language: Английский

Citations

3