UV light enabled methylation of quinoline-2-thione using dimethyl sulfoxide to give quinoline methyl sulfide

Wang, Xi Cun; Liu, Xiaojun; Zhang, Xi; Cao, Bao-Qian; Quan, Zheng‐Jun

doi:10.1016/j.tetlet.2018.11.008

Cited by 12 publications

(1 citation statement)

References 57 publications

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“…The same year, Wang et al. reported the synthesis of quinoline methyl sulfides 19 via the thiomethylation of quinoline‐2‐thiones 18 with DMSO 1 as the methyl source, under UV light in the presence of DBU as a base (Scheme ). A wide range of quinoline‐2(1 H )‐thiones 18 containing electron‐withdrawing, electron‐donating and halide (F, Cl) groups was screened to afford the corresponding quinoline methyl sulfides 19 in good to high yields (82–92%).…”

Section: Single Synthonmentioning

confidence: 99%

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent

et al. 2019

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Dimethyl sulfoxide (DMSO) has had a long history of use as a polar solvent and active pharmaceutical ingredient in the past decades. However, in this decade DMSO has attracted the attention of scientists as a source of oxygen, carbon or sulfur in a wide range of organic reactions. In this review, we have summarized and classified the latest findings in this area based on applications of DMSO as a single or a dual synthon.

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Section: Single Synthonmentioning

confidence: 99%

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent

et al. 2019

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The Applications of Dimethyl Sulfoxide as a One‐Carbon Source in Organic Synthesis

Li¹,

Wu²

2022

The Chemical Transformations of C1 Compounds

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Redox‐Divergent Construction of (Dihydro)thiophenes with DMSO

Liu

Zhao

et al. 2021

Angewandte Chemie

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Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules.I nspired by the redox diversity of these features in nature,w ed emonstrate herein ar edox-divergent construction of dihydrothiophenes,thiophenes,and bromothiophenes from the respective readily available allylic alcohols,d imethyl sulfoxide (DMSO), and HBr.T he redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr.M echanistic studies suggest that DMSO simultaneously acts as an oxidant and as ulfur donor.T he synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations,i ncluding the preparation of bioactive and functional molecules.

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UV light enabled methylation of quinoline-2-thione using dimethyl sulfoxide to give quinoline methyl sulfide

Cited by 12 publications

References 57 publications

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent

The Applications of Dimethyl Sulfoxide as a One‐Carbon Source in Organic Synthesis

Redox‐Divergent Construction of (Dihydro)thiophenes with DMSO

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