C3-selective C–H thiolation of quinolines <i>via</i> an <i>N</i>-arylmethyl activation strategy

Li, Shun; Tang, Juan; Fu, Yi-Hua; Zheng, Xueli; Li, Ruixiang; Su, Zhishan; Fu, Haiyan; Chen, Hua

doi:10.1039/d3qo00244f

Cited by 9 publications

(1 citation statement)

References 66 publications

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“…Chen and co‐workers reported an N ‐arylmethyl activation strategy realizing the direct C3‐H thioetherification reaction of quinolines (Scheme 1a). [ 8 ] Although this method was metal‐free, it still required higher temperature and a longer reaction time. Hence, developing a green and mild synthetic strategy for the C3‐thioetherification of quinolines is still in high demand.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Electrochemical Cascade Annulation for the Synthesis of 3‐Sulfanylquinoline Derivatives Under Mild Conditions

Li,

Guo,

Chen

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAn efficient electrochemical approach has been developed for the construction of 3‐sulfanylquinoline derivatives by treating phenylethynylbenzoxazinanones with disulfides in an undivided cell. The protocol provided a convenient route to functionalized quinolines with good functional group tolerance. Moreover, it does not require any metal catalysts or additives, furnishing a series of biological quinolines in moderate to good yields.

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Section: Background and Originality Contentmentioning

confidence: 99%

Electrochemical Cascade Annulation for the Synthesis of 3‐Sulfanylquinoline Derivatives Under Mild Conditions

Li,

Guo,

Chen

et al. 2024

Chin. J. Chem.

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Synthesis of Trifluoromethylthiolated Quinolinones via Trifluoromethanesulfanamide‐Induced Electrophilic Intramolecular Cyclization of N‐Arylpropynamides

Xu,

Sun,

Zhao

et al. 2023

Adv Synth Catal

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The reaction of N‐arylpropynamides with the commercially available trifluoromethanesulfanamide in the presence of BiCl3 was found to afford quinolin‐2‐ones in a selective manner via electrophilic trifluoromethylthiolation enabled by the in‐situ generated CF3S−Cl and the followed intramolecular cyclization. Differing from the existing analogous cyclization route that solely produces spiro[4,5]trienones, this alternative approach exclusively affords the biologically interesting quinolin‐2‐ones as the major products.

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Bis(phenylsulfonyl)sulfide as a Bifunctional Single‐Sulfur Source for the Rapid Assembly of Unsymmetric Diaryl Sulfides Enabled by Copper Catalyst

Wang,

Zhou,

Huang

et al. 2024

ChemistrySelect

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Rapid access to unsymmetrical diaryl sulfides through a bifunctional single‐sulfur source is a very attractive strategy. Here we report the utilization of bis(phenylsulfonyl)sulfide as a bielectrophilic sulfide platform molecule for chemoselective and sequential installation of two different aryl nucleophiles by twice copper‐catalyzed Chan–Lam‐type cross couplings to access diverse unsymmetrical diaryl sulfides. This strategy demonstrates good tolerance to a wide range of aryl boronic acids under different metal catalysts, good functional group compatibility, as well as the extension to the modification of complex bioactive molecules.

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C3-selective C–H thiolation of quinolines via an N-arylmethyl activation strategy

Abstract: An N-arylmethyl activation strategy has been developed to solve the challenging problems associated with the direct C3-H thiolation reaction of quinolines, including trifluoromethylthiolation, arylthiolation, alkylthiolation and phenylselenylation. The relevant theoretical...

Cited by 9 publications

References 66 publications

Electrochemical Cascade Annulation for the Synthesis of 3‐Sulfanylquinoline Derivatives Under Mild Conditions

Electrochemical Cascade Annulation for the Synthesis of 3‐Sulfanylquinoline Derivatives Under Mild Conditions

Synthesis of Trifluoromethylthiolated Quinolinones via Trifluoromethanesulfanamide‐Induced Electrophilic Intramolecular Cyclization of N‐Arylpropynamides

Bis(phenylsulfonyl)sulfide as a Bifunctional Single‐Sulfur Source for the Rapid Assembly of Unsymmetric Diaryl Sulfides Enabled by Copper Catalyst

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