Nickel(II)-Catalyzed Oxygen Transfer Reaction of <i>N</i>-Vinyl Nitrones to Prepare 2-(Pyridin-2-yl)ethanols

Zou, Ning; Lan, Jing-Xuan; Yan, Gong-Gui; Liang, Cui; Su, Gui‐Fa; Mo, Dong‐Liang

doi:10.1021/acs.orglett.0c02947

Cited by 9 publications

(3 citation statements)

References 44 publications

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“…amine 9 mediated by copper, 11 and nickel-mediated formation of the pyridine ring using N-vinyl nitrones 10 (Scheme 1). 12 Installation of a 2-aryl group on a pyridine moiety is usually achieved through reaction of pyridine N-oxides 13 with Grignard reagents, 14,15 and from arylboronic acids by Suzuki-Miyaura coupling. 16 In this study, a series of 2-arylsubstituted 7,8-dihydroquinolin-6(5H)-ones were prepared by a novel, facile, and metal-free methodology and the potential of the obtained 2-aryl-7,8-dihydroquinolin-6(5H)ones as cytotoxic agents was evaluated against a cell line panel.…”

Section: Paper Synthesismentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Blé González,

Martínez,

Bautista

et al. 2023

Synthesis

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Herein we present a facile four-step synthetic method for the synthesis of novel 2-aryl-substituted 7,8-dihydroquinolin-6(5H)-ones as cytotoxic agents. The key step was the use of Mannich salts derived from acetophenones as a Michael acceptor in the reaction with cyclohexane-1,4-dione monoethylene acetal to give 1,5-dicarbonyl compounds that were treated with ammonium acetate to give the 7,8-dihydroquinolin-6(5H)-ones. The cytotoxic activity of the synthesized compounds was evaluated against seven cell lines. The observed data showed good selectivity for chronic myeloid leukemia line K-562. The synthetic route was simple and applicable to various functional group containing substrates. These types of compounds may be utilized as lead compounds in cancer research and drug discovery.

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Section: Paper Synthesismentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Blé González,

Martínez,

Bautista

et al. 2023

Synthesis

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“…同年, 该小组 [40] 在此基础上以 N-烯基-α,β-不饱和 20 Proposed mechanism of constructing ninemembered heterocycles endoperoxides from N-vinyl-α,βunsaturated nitrones through visible light 2.2.2 N-烯基-α,β-不饱和硝酮构建吡啶化合物 2018 年, 莫冬亮课题组 [41] 2020 年, 该课题组 [43] 还发展了镍催化 N-烯基-α,β-不饱和硝酮的分子内氧转移反应, 合成了多取代吡啶醇化合物 69. 通过该方法经三步反应以 36%产率得到吲哚生物碱类化合物.…”

Section: N-烯基-αβ-不饱和硝酮与亚甲基环丙烷发生[3＋2]环加unclassified

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Zou¹,

Qin²,

Wang³

et al. 2021

Chinese Journal of Organic Chemistry

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Nitrones, served as one of the most important 1,3-dipoles in organic synthetic chemistry, can participate in various organic synthetic reactions to synthesize various heterocyclic compounds, such as nucleophilic addition, cycloaddition reaction, rearrangement reaction, C-H bond activation, etc. They are very important organic building blocks for the further construction of complex molecules. In recent years, α,β-unsaturated nitrone has attracted widespread attention from synthetic chemists because of its α,β-unsaturated bond containing rich chemical transformations, and can take part in various new chemical conversions to construct new structural heterocyclic compounds. The new strategies for the preparation of α,β-unsaturated nitrones in the past ten years, and their applications to construct nitrogen heterocyclic compounds, including O-transfer reaction, addition of nucleophiles and radical reagents, and various cycloaddition reactions, are reviewed.

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“…Nitrones, as extensively used 1,3-dipoles, have served as powerful reagents to access various significant azaheterocycles by cycloaddition reaction . In recent years, N -vinyl nitrone has been received much attention because of their ease in further transformations, such as electrocyclization, O -transfer reaction, and cycloaddition reaction . Based on the studies of N -vinyl nitrones in our group, we found that N -vinyl-α,β-unsaturated nitrones could participate in cycloaddition/rearrangement to access nine-membered azahetereocycles by reacting with various electrophiles .…”

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confidence: 99%

Synthesis of 1,2,4-Oxadiazolines through Deoxygenative Cyclization of N-Vinyl-α,β-Unsaturated Nitrones with in Situ Generated Nitrile Oxides from Hydroxamoyl Chlorides

Nong

Shi

et al. 2022

Org. Lett.

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A variety of 1,2,4-oxadiazoline derivatives were synthesized in moderate to good yields through a deoxygenative cyclization cascade reaction of N-vinyl-α,β-unsaturated nitrones and hydroxamoyl chlorides. Mechanistic studies revealed that the reaction underwent double additions of nitrile oxides to N-vinyl-α,β-unsaturated nitrones, sequential elimination, and intramolecular cyclization to afford 1,2,4-oxadiazolines. Alternatively, 1,2,5-oxadiazolines were also obtained as major products in i-PrOH solvent through [3 + 3] cycloaddition and selective [3,3]-rearrangement. Moreover, the prepared 1,2,4-oxadiazolines were easily converted to polysubstituted pyrroles under thermal conditions.

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Nickel(II)-Catalyzed Oxygen Transfer Reaction of N-Vinyl Nitrones to Prepare 2-(Pyridin-2-yl)ethanols

Cited by 9 publications

References 44 publications

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Synthesis of 1,2,4-Oxadiazolines through Deoxygenative Cyclization of N-Vinyl-α,β-Unsaturated Nitrones with in Situ Generated Nitrile Oxides from Hydroxamoyl Chlorides

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