Selective C<sub>3</sub>-nitrosation of imidazopyridines using AgNO<sub>3</sub> as the NO source

Kudale, Vishal Suresh; Chu, Ching-Piao; Wang, Jhi-Joung

doi:10.1039/d2nj02115c

Cited by 4 publications

(1 citation statement)

References 53 publications

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“…Next, based on the abovementioned experimental results and the literatures, ,, a possible radical mechanism was proposed (Figure ). First, TBN is excited under visible-light irradiation and decomposes into a tert -butoxy radical and a nitroso radical.…”

Section: Resultsmentioning

confidence: 99%

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Qiao,

Zhao,

Zhu

et al. 2024

J. Org. Chem.

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This study reports a protocol for the highly regioselective photocatalyzed C−H nitrosylation of imidazo[1,2-a]pyridine scaffolds at the C3 position under a combination of visible-light irradiation and continuous flow without any external photocatalyst. This protocol involves mild and safe conditions and shows good tolerance to air and water along with excellent functional group compatibility and site selectivity, generating various 3nitrosoimidazo[1,2-a]pyridines in excellent yields under photocatalyst-, oxidant-, and additive-free conditions.Notably, the proposed nitrosylation reaction, which introduces the chromophore NO into imidazo[1,2-a]pyridine scaffolds, occurs efficiently under visible-light irradiation without any additional photocatalyst owing to the intense light-absorption characteristics of the nitrosylation products. This study could guide future studies on the development of green organic-synthesis strategies with a wide variety of potential applications.

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Section: Resultsmentioning

confidence: 99%

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Qiao,

Zhao,

Zhu

et al. 2024

J. Org. Chem.

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Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

2024

Adv Synth Catal

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Imidazoheterocycles have extensive applications in the pharmaceutical industry and agrochemicals. A comprehensive overview has been provided on the current advancements in electrochemical functionalization, which has been classified ten different types of reactions. Electrochemical synthesis has emerged as a highly effective method for producing organic molecules, especially in the context of sustainable development. Employing electrons as the traceless oxidant, several C–H functionalization reactions of imidazo‐fused heterocycles have been achieved at either the C3 or C5 positions. Electrons may serve as the reducing agent to synthesize pyridine rings that are either partially or fully saturated in imidazo[1,2‐a]pyridines. The purpose of the review is to attract the interest of the scientific community and promote additional research on the functionalization of imidazoheterocycles using electrochemical methods.

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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Selective C₃-nitrosation of imidazopyridines using AgNO₃ as the NO source

Abstract: We developed a novel method for selective radical nitrosation of imidazo[1, 2-a]pyridine derivatives using AgNO3 as a NO source. Moreover, one-pot and sequential one-pot strategies are effective in standard conditions....

Cited by 4 publications

References 53 publications

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

Five-membered ring systems: with more than one N atom

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Selective C3-nitrosation of imidazopyridines using AgNO3 as the NO source

Abstract: We developed a novel method for selective radical nitrosation of imidazo[1, 2-a]pyridine derivatives using AgNO3 as a NO source. Moreover, one-pot and sequential one-pot strategies are effective in standard conditions....

Cited by 4 publications

References 53 publications

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Photocatalyzed C3–H Nitrosylation of Imidazo[1,2-a]pyridine under Continuous Flow and External Photocatalyst-, Oxidant-, and Additive-Free Conditions

Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

Five-membered ring systems: with more than one N atom

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Selective C₃-nitrosation of imidazopyridines using AgNO₃ as the NO source