Iodine/persulfate-promoted site-selective direct thiolation of quinolones and uracils

Beukeaw, Danupat; Noikham, Medena; Yotphan, Sirilata

doi:10.1016/j.tet.2019.130537

Cited by 23 publications

(16 citation statements)

References 71 publications

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“…Beukeaw and co‐workers [116] extended the applicability of iodine by combining it with K 2 S 2 O 8 in a metal‐free regioselective C‐3 and C‐5 sulfenylation of 4‐quinolones ( 54 ) and uracils ( 55 ) respectively (Scheme 18). The optimized condition screened initially with different halogen inducers, oxidizing agents and various solvents was applied successfully to differently substituted 4‐quinolones/uracil.…”

Section: Sulfenylationmentioning

confidence: 99%

“…The regioselectivity was confirmed when sulfenylation was not observed in case 3‐methyl substituted quinolone or 5‐methyl substituted uracil under optimized condition. Incomplete quenching of the model reaction in presence of TEMPO brought ambiguity in the mechanistic approach [116] …”

Section: Sulfenylationmentioning

confidence: 99%

“…The source of thiomethyl group was confirmed when a reaction of 2-phenylimidazo[1,2a]pyridine (13) and phenylacetylene (37) 53) and iodine was regenerated by the oxidation of HI with DMSO (Scheme 17). [115] Beukeaw and co-workers [116] extended the applicability of iodine by combining it with K 2 S 2 O 8 in a metal-free regioselective C-3 and C-5 sulfenylation of 4-quinolones (54) and uracils (55) respectively (Scheme 18). The optimized condition screened initially with different halogen inducers, oxidizing agents and various solvents was applied successfully to differently substituted 4-quinolones/uracil.…”

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confidence: 99%

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Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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Transition metal‐free sulfenylation of C−H bonds for C−S bond formation has recently emerged as sustainable protocols for the functionalisation of various molecules. Researchers have extensively developed such protocols for the construction of biologically relevant sulfur scaffolds. There has been a gradual shift from metal‐catalyzed to metal‐free C−S bond formation methodologies, because the latter offer environmentally benign and inherently safe access to novel synthetic routes in organic chemistry. The present review offers a dynamic discussion on recent advances in transition metal‐free C−S bond formation via C−H bond functionalization using different surrogate sulfenylating reagents. The review has comprehensively been devoted to radical and ionic mechanistic approaches. Some simple and eco‐friendly reagents for sulfenylation viz. tertbutyl hydrogen peroxide (TBHP), hydrogen peroxide (H2O2), iodine/potassium persulphate (I2/K2S2O8), inorganic bases, strong organic acids, iodine, I2/triphenyl phosphine (PPh3), N‐chlorosuccinamide (NCS), N‐bromosuccinamide (NBS), potassium iodate (KIO3), I2/bovine serum albumin (BSA), tetrabutyl ammonium iodide (TBAI)/HBr and graphene oxide along with their mechanistic approach has been detailed in this review. Moreover, modern methods for the C−S bond formation i. e., biocatalyst, electrochemical and visible light induced sulfenylation, and traditional sulfenylation methodologies have also been incorporated.

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Section: Sulfenylationmentioning

confidence: 99%

Section: Sulfenylationmentioning

confidence: 99%

mentioning

confidence: 99%

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Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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“…[58] Organic sulfur-containing molecules especially thioether have been widely recognized in the field of medicinal chemistry due to their wide array of biological activities. Beukeaw et al developed a simple, efficient, and metal-free synthetic protocol for the synthesis of S-linked 4-quinolones (60) via site-selective direct thiolation of quinolones (58) with disulfide (59) or thiol in the presence of iodine/persulfate system which promoted the CÀ S coupling reaction. The reaction was optimized for reagents, oxidants, and solvents affecting the transformation of the substrate to the final product.…”

Section: Synthesis Of 4-quinolones Using An Organic/inorganic Catalystmentioning

confidence: 99%

“…The proposed mechanism of the reaction is shown below in figure 15. [59] Ghosh and co-workers reported a unique and efficient metal-free methodology for the synthesis of 3-thio/selenocyanates derivatives of 4-quinolones. Reaction conditions were optimized for oxidant, solvent, and temperature conditions.…”

Section: Synthesis Of 4-quinolones Using An Organic/inorganic Catalystmentioning

confidence: 99%

Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

2020

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The ubiquitous presence of 4-quinolones and its derivatives in a wide range of natural as well as synthetic drug molecules made them molecule of utmost importance for organic and medicinal chemists. Their wide array of biological activities such as antimicrobial, anticancer, anti-HIV, genitourinary infection, antifilarial, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Moreover, they are valuable intermediates for the synthesis of various fused heterocyclic compounds of synthetic and medicinal importance. Considering their array of synthetic and biological importance, new strategies for the synthesis of 4-quinolones and their derivatives have been designed and successfully demonstrated by researchers around the globe. The present review covers recent advances in the synthetic chemistry of 4quinolones since 2015 along with an insight into their mechanistic studies. We hope that the review article will serve as a valuable tool for the scientific community engaged in the synthesis and utilization of 4-quinolones and their derivatives.

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Iodine‐DMSO‐Promoted Oxygenation of Indoles: Synthesis of Isatin and Isoindigo

et al. 2022

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Oxygenation/oxidative self-coupling of indole are performed to obtain isatin and isoindigo in the absence of metal catalysts. Iodine-DMSO is used to synthesize isatin whereas Iodine-DMSO-K 2 S 2 O 8 combination is used for isoindigo synthesis directly from indole in a single step. Though several methods are known for isatin synthesis from indole, most of them use large quantity of oxidants or metal catalyzed. Moreover, the primary existing process for the synthesis of isoindigo is the condensation of isatin and oxindole in the presence of an acid catalyst. But this method provides isoindigo derivatives directly from indoles. A plausible mechanism is also proposed based on the various control experiments which indicate that both the reactions proceed via radical route. It is also observed that oxygen atoms of isatin and isoindigo come from water molecule and DMSO.

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Iodine/persulfate-promoted site-selective direct thiolation of quinolones and uracils

Cited by 23 publications

References 71 publications

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Recent Developments in the Synthetic Strategies of 4‐Quinolones and Its Derivatives

Iodine‐DMSO‐Promoted Oxygenation of Indoles: Synthesis of Isatin and Isoindigo

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