Silver-catalyzed nitrosation and nitration of aromatic amides using NOBF4 DOI

Sa Li,

Wentao Liu,

Xiao‐Feng Xia

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(47), P. 9428 - 9432

Published: Jan. 1, 2023

An efficient strategy for divergent aromatic ring nitrosation and nitration of amides was developed using NOBF 4 as the electrophile under silver-catalyzed conditions.

Language: Английский

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 Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N‐Nitrosation of Secondary Amines DOI
Ying Wang, Shiqi You,

Mengyao Ruan

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(22), P. 3289 - 3293

Published: May 11, 2021

Abstract We report herein on the electrochemical N ‐nitrosation of secondary amines using widely available sodium/potassium nitrite as a nitrosating agent. This approach not only eliminates need for combination and strong acid but also has good functional group tolerance. The reaction is compatible with late‐stage modification pharmaceutical compounds could be conducted in gram scale high efficiency. Preliminary mechanistic studies indicate that occurs via anodic oxidation KNO 2 into an NO radical which then transformed + cation.

Language: Английский

Citations

10
Non‐Conventional Methodologies for the Synthesis of N‐Nitrosamines DOI Open Access
Rojan Ali, Campbell S. Wolfe, Thomas Wirth

et al.

Chemistry - Methods, Journal Year: 2024, Volume and Issue: 4(4)

Published: March 4, 2024

Abstract N ‐Nitrosamines acting as contaminants in our environment is a topic of increasing concern. Detection methods are required, necessitating analytical standards. Herein, we discuss some conventional methodologies to prepare ‐nitrosamines and compare them with unconventional pathways towards their synthesis. These often more environmentally benign safer.

Language: Английский

Citations

1
Synthesis of Nitrated N‐Alkyl Anilines Using N‐Nitroso Anilines as a Self‐Providing Nitro Group Source DOI
Yuxian Zhang, Shuwei Zhang, Zheng Sun

et al.

Asian Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 8(12), P. 2205 - 2208

Published: Nov. 13, 2019

Abstract In the presence of dioxygen, an efficient synthesis nitrated N‐alkyl anilines was realized using N‐nitroso as starting material. According to mechanistic study, served a self‐providing nitro group source promote direct nitration N‐alkylanilines, avoiding undesired protection amine group.

Language: Английский

Citations

10
Selective C3-nitrosation of imidazopyridines using AgNO3 as the NO source DOI
Vishal Suresh Kudale,

Ching-Piao Chu,

Jeh‐Jeng Wang

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(31), P. 15200 - 15204

Published: Jan. 1, 2022

We developed a novel method for selective radical nitrosation of imidazo[1, 2- ]pyridine derivatives using AgNO 3 as NO source.

Language: Английский

Citations

4
tert-Butyl Nitrite as a Privileged Reagent for C-H Bond (Sub)Nitration Reaction in Organic Synthesis DOI

Jiaoli Ma,

P. Chen,

Junli Zeng

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14128 - 14139

Published: Jan. 1, 2024

Due to its low price, mild reaction conditions and high reactivity, tert -butyl nitrite, as a green novel nitrification reagent, has attracted much attention made promising progress.

Language: Английский

Citations

0
Metal‐Free Nitration of Indazoles with tert‐Butyl Nitrile in Air to Prepare 3‐Nitroindazoles and 3‐Aminoindazoles DOI
Xinyue Zhang, Rui Jiang, X. PAN

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 8, 2024

Comprehensive Summary A variety of 3‐nitroindazoles and 3‐aminoindazoles were prepared in good to excellent yields with high regioselectivity through TBN‐mediated nitration at the C3‐position indazoles under air conditions sequential reduction. Mechanistic studies revealed that TBN played crucial roles produce •NO 2 radical source presence C3‐nitration was initiated by N1‐nitration migration NO group C3‐position. Moreover, this method could be easily applied gram scalable synthesis ibuprofen ciprofibrate‐derived 3‐aminoindazoles. The present highlights as mild oxidant, metal‐free indazole, N—N bond formation cleavage, late‐stage modification drugs.

Language: Английский

Citations

0
Silver-catalyzed nitrosation and nitration of aromatic amides using NOBF4 DOI

Sa Li,

Wentao Liu,

Xiao‐Feng Xia

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(47), P. 9428 - 9432

Published: Jan. 1, 2023

An efficient strategy for divergent aromatic ring nitrosation and nitration of amides was developed using NOBF 4 as the electrophile under silver-catalyzed conditions.

Language: Английский

Citations

0