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 10 publications

(3 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…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 .…”

mentioning

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.

Self Cite

View full text Add to dashboard Cite

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.

show abstract

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

Cited by 10 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

Contact Info

Product

Resources

About