Metal‐Free Chemoselective Oxidation of 4‐Methylquinolines into Quinoline‐4‐Carbaldehydes

Xu, Jincheng; Li, Yang; Ding, Tianling; Guo, Hao

doi:10.1002/asia.202100704

Cited by 6 publications

(4 citation statements)

References 65 publications

(1 reference statement)

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“…Six compounds ( 3aa , 3r ′, 3s , 5s, 6r ′, 6s ) were evaluated for their inhibition of the cell TPC-1 viability in vitro by the CCK-8 assay (Scheme ). The test results showed that most of them have stronger in vitro growth inhibitory activities than cisplatin (IC 50 = 0.85 μM), with IC 50 values of 0.50, 0.27, 0.38, 0.31, 0.19, and 0.90 μM. In particular, 6r ′ performed far better than cisplatin, which will be contributed to future drug design due to the great antineoplastic potential exhibited in this skeleton.…”

Section: Resultsmentioning

confidence: 99%

Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination

Liu

et al. 2023

J. Org. Chem.

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A visible light-induced diastereoselective synthesis of trifluoromethylated cyclobutane derivatives is described, consisting of [2+2]-photocycloaddition and water-assisted hydrodebromination by one pot. Quinolinones, isoquinolinones, and coumarins are able to participate in this one-pot process with 1-bromo-1-trifluoromethylethene. In addition, stereodefined trisubstituted trifluoromethylated cyclobutane alcohols, carboxylic acids, and amines can be obtained in a straightforward manner through the ring opening of lactone or lactam without the loss of original high diastereoselectivity given by the water–tristrimethylsilylsilane coordination. The antineoplastic bioactivities of those compounds are also well studied, which exhibit great antineoplastic potential comparable to cisplatin. In the proposed mechanism, thioxanthone (TX) serves as a dual catalyst and a radical chain pathway may be involved in the hydrodebromination process.

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Section: Resultsmentioning

confidence: 99%

Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination

Liu

et al. 2023

J. Org. Chem.

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“…65 A potential alternative approach could be based off of the work of Guo, who reported the use hypervalent iodine for the production of aldehydes from methylquinolines, proposed to occur through a dearomatization mechanism. 66 In the case of secondary carbons, acetoxylation was observed instead (Fig. 2d).…”

Section: Introductionmentioning

confidence: 94%

Site-selective benzylic C–H hydroxylation in electron-deficient azaheterocycles

Kaur,

Cooper,

Van Humbeck

2024

Org. Biomol. Chem.

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“…55 A potential alternative approach could be based off of the work of Guo, who reported the use hypervalent iodine for the production of aldehydes from methylquinolines, proposed to occur through a dearomatization mechanism. 56 In the case of secondary carbons, acetoxylation was observed instead (Fig. 2d).…”

mentioning

confidence: 94%

Site-Selective Benzylic C–H Hydroxylation in Electron-Deficient Azaheterocycles

Kaur,

Cooper,

Van Humbeck

2024

Preprint

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Benzylic C–H bonds can be converted into numerous functional groups, often by mechanisms that involve hydrogen atom transfer at the key bond breaking step. The abstracting species is most often an electrophilic radical, which makes these reactions best suited to electron-rich C–H bonds to achieve appropriate polarity matching. Thus, electron deficient systems such as pyridine and pyrimidine are relatively unreactive, and relatively underrpresented in substrate scopes. In this report, we describe a new method for benzylic hydroxylation—essentially an unknown reaction in the case of pyrimidines—that makes use of an iodine(III) reagent to affords very high selectivity towards electron-deficient azaheterocycles in substrates with more than one reactive position and prevents over-oxidation to carbonyl products. The identification of key reaction byproducts supports a mechanism that involves radical coupling in the bond forming step.

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Metal‐Free Chemoselective Oxidation of 4‐Methylquinolines into Quinoline‐4‐Carbaldehydes

Cited by 6 publications

References 65 publications

Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination

Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination

Site-selective benzylic C–H hydroxylation in electron-deficient azaheterocycles

Site-Selective Benzylic C–H Hydroxylation in Electron-Deficient Azaheterocycles

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