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

Pathways for N-Nitroso Compound Formation: Secondary Amines and Beyond DOI

Rocío López‐Rodríguez,

James A. McManus,

Natasha S. Murphy

et al.

Organic Process Research & Development, Journal Year: 2020, Volume and Issue: 24(9), P. 1558 - 1585

Published: July 28, 2020

Recent drug recalls (e.g., valsartan and ranitidine) linked to the discovery of nitrosamine impurities have led increased regulatory scrutiny in manufacturing process marketed medicines, notably for determining any sources risk (or related N-nitroso compound) formation within process. This review seeks aid assessment through identifying known conditions reactants which compounds can be formed.

Language: Английский

Citations

90

Recent advances in nitro-involved radical reactions DOI Open Access
Jiapian Huang,

Feng Ding,

Pornchai Rojsitthisak

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(18), P. 2873 - 2898

Published: Jan. 1, 2020

Significant progress in the chemistry of nitro radicals has been witnessed past decades, providing efficient and rapid access to nitro-containing compounds. This review describes recent advances nitro-involved radical reactions, summarizes various transformations.

Language: Английский

Citations

47

Antibacterial and antiviral activities and action mechanism of flavonoid derivatives with a benzimidazole moiety DOI Creative Commons

Mei Chen,

Shijun Su,

Qing Zhou

et al.

Journal of Saudi Chemical Society, Journal Year: 2021, Volume and Issue: 25(2), P. 101194 - 101194

Published: Jan. 9, 2021

A class of novel benzimidazole-containing flavonoid derivatives were constructed. Antibacterial bioassay showed that most the target compounds displayed good inhibitory effects against Xanthomonas axonopodis pv. citri (Xac), Ralstonia solanacearum (Rs) and oryzae (Xoo). Remarkably, compound 4e outstanding antibacterial activity Rs, with EC50 14.5 µg/mL, which was better than thiodiazole-copper (118.9 µ/mL), bismerthiazol (55.1 µg/mL) myricetin (82.3 µg/mL). At same time, mechanism confirmed by scanning electron microscopy (SEM). Antiviral results demonstrated 4n remarkable curative, protective inactivating activities tobacco mosaic virus (TMV), a 500 µg/mL effective concentration 54.1, 57.6 75.3%, respectively. The test revealed these values or close to ningnanmycin (49.0, 55.8 82.7%, respectively). Microscale thermophoresis (MST) also binding TMV coat protein (TMV-CP) gave Kd value 1.049 ± 0.582 µmol/L, (1.058 0.286 µmol/L). This study are promising agricultural antiviral agents.

Language: Английский

Citations

37

Electrochemical sensing of acetaminophen, phenylephrine hydrochloride and cytosine in drugs and blood serum samples using β-AgVO3/ZrO2@g-C3N4 composite coated GC electrode DOI
E. Murugan,

A. Poongan,

A. Dhamodharan

et al.

Journal of Molecular Liquids, Journal Year: 2022, Volume and Issue: 348, P. 118447 - 118447

Published: Jan. 4, 2022

Language: Английский

Citations

24

Electrochemical Nonacidic N‐Nitrosation/N‐Nitration of Secondary Amines through a Biradical Coupling Reaction DOI
Jiping Zhao,

Lujia Ding,

Pengcheng Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(22), P. 5036 - 5043

Published: June 23, 2020

Abstract An acid‐free N‐nitrosation/nitration of the N−H bonds in secondary amines with Fe(NO 3 ) ⋅ 9H 2 O as nitroso/nitro source through an electrocatalyzed radical coupling reaction was developed. Cyclic aliphatic and N‐heteroaromatic compounds were N‐nitrosated N‐nitrated, respectively, under mild conditions. Control competition experiments, well kinetic studies, demonstrate that N‐nitrosation N‐nitration involve two different pathways involving N + . radicals. Moreover, electrocatalysis method enables preferential activation bond over electrode thus provides high selectivity for specific atoms. Finally, this strategy exhibits a broad scope green straightforward approach to generate useful ‐nitroso/nitro good yields. magnified image

Language: Английский

Citations

28

Divergent g-C3N4-catalyzed Reactions of Quinoxalin-2(1H)-ones with N-Aryl Glycines under Visible Light: Solvent-Controlled Hydroaminomethylation and Annulation DOI
Ya‐Feng Si, Xiaolan Chen, Xiaoyang Fu

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2020, Volume and Issue: unknown

Published: July 16, 2020

An effective and simple visible light-induced heterogeneous g-C3N4-catalyzed decarboxylative reaction of quinoxalin-2(1H)-ones with N-aryl glycines was developed. When the performed in DMSO/H2O EtOH, products dihydroquinoxalin-2(1H)-ones tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones were unprecedentedly obtained good yields, respectively. This solvent-dependent system offers advantages, including easy operation, short time, high chemoselectivity, a recyclable catalyst, metal-/base-/oxidant-free, mild conditions.

Language: Английский

Citations

18

Synthesis and application of α-carbonyl nitrile oxides DOI
Xuanhua Guo, Guangqiang Xu, Li Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(17), P. 2467 - 2473

Published: Jan. 1, 2020

A strategy has been developed to synthesize α-carbonylfuran and isoxazole using tert-butyl nitrite (TBN) as a nitrogen source.

Language: Английский

Citations

17

Modified NAP test: A simple and Responsive Nitrosating Methodology for Risk Evaluation of NDSRIs DOI
Nitish Sharma,

Rashi Patel,

Tejaswini Bothara

et al.

Journal of Pharmaceutical Sciences, Journal Year: 2023, Volume and Issue: 112(5), P. 1333 - 1340

Published: March 4, 2023

Language: Английский

Citations

5

Copper-catalyzed,N-auxiliary group-controlled switchable transannulation/nitration initiated by nitro radicals: selective synthesis of pyridoquinazolones and 3-nitroindoles DOI
Adedamola Shoberu, Chengkun Li, Haifeng Qian

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(20), P. 5821 - 5830

Published: Jan. 1, 2021

Within the scope of nitration reactions, efficiency sensitive heteroaromatics such as indoles is often eroded by various competitive oxidative decomposition pathways.

Language: Английский

Citations

11

2‐Methoxyethyl Nitrite as a Reagent for Chemoselective On‐Water Nitration DOI
Taku Kitanosono,

Airu Hashidoko,

Yasuhiro Yamashita

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(16)

Published: May 25, 2022

An on-water approach has been developed that allows a nitration of tyrosines and phenols under mild conditions. We envisioned the assembly tyrosine/tyrosyl radical couples with interfacial water molecules would realize biomimetic stacking hydrogen atom transfer (HAT) transition state to facilitate electron-transfer process. The optimal organic nitrite, 2-methoxyethyl resulted in rapid coupling tyrosyl radicals ⋅NO2 at oil-water interface afford nitrated phenols. Many characteristics found our strategy are distinct from other complementary systems include nitration. These enticing roles reaction process introduce new avenues explore design synthetic chemistry systems.

Language: Английский

Citations

8