Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

New Journal of Chemistry, Год журнала: 2024, Номер 48(17), С. 7614 - 7638

Опубликована: Янв. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Язык: Английский

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Adamantane-Quinoxalone Hybrids: Precision Chemotypes and Their Molecular Mechanisms in Acute Myeloid Leukemia

Journal of Medicinal Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 31, 2025

Acute myeloid leukemia (AML) is an aggressive blood cancer with a poor prognosis, especially when diagnosed late. Around 10–15% of cases involve the specific chromosomal abnormality t(8;21), which drives uncontrolled cell proliferation and contributes to disease onset. Despite advances in AML research treatment protocols, outcomes for t(8;21) remain stagnant, as patients receive standard, nonspecific chemotherapies. This one-size-fits-all approach targets both cancerous healthy cells, leading unwanted toxicity highlighting urgent need targeted therapies. In this study, we present precision chemotype based on quinoxalone-tethered adamantane framework developed via metal- light-free protocol. The compound selectively inhibits induces death by disrupting growth metabolic pathways, demonstrated through bioassays, RNA sequencing, proteomic analysis. Notably, it spares other leukemic solid underscoring its specificity potential therapy AML.

Язык: Английский

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Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1H)-ones via Electron Donor–Acceptor Complexes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13339 - 13350

Опубликована: Авг. 31, 2023

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation photoactivated electron donor–acceptor complex between present method provides mild environmentally friendly protocol that exhibits good atom economy excellent functional group tolerance to obtain library biologically significant α-aminomethylated in yields.

Язык: Английский

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Visible-Light-Promoted Deoxygenative Alkylation of Quinoxalin-2(1H)-ones with Activated Alcohols

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6334 - 6344

Опубликована: Апрель 15, 2024

A one-pot strategy for deoxygenative alkylation of alcohols with quinoxalin-2(1H)-ones was developed by using xanthate salts as alcohol-activating groups radical generation in the presence tricyclohexylphosphine under visible-light-promoted conditions. The remarkable features this reaction include a broad substrate scope, excellent functional group tolerance, mild conditions, and simple operation. Moreover, synthetic utility validated success two-step reactions, scale-up synthesis, chemoselective monodeoxygenation diols.

Язык: Английский

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Visible Light‐Enabled Decarboxylative Alkylation of Quinoxalin‐2(1H)‐ones using Alkyl Carboxylic Acids via Energy Transfer Process

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2735 - 2741

Опубликована: Апрель 20, 2024

Abstract Here in, we describe the photochemical decarboxylative alkylation of quinoxalin‐2(1 H )‐ones using commercially accessible carboxylic acids with oxygen as sole oxidant through energy transfer process. The coupling diverse array alkyl (1° to 3°) and bioactive is successfully accomplished achieve desired alkylated products.

Язык: Английский

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Metal‐Free Direct C3−H Alkylation and Arylation of Quinoxalin‐2(1H)‐Ones with Inert Alkyl and Aryl Chlorides

Chemistry - A European Journal, Год журнала: 2023, Номер 29(47)

Опубликована: Июнь 7, 2023

In the present manuscript, we reported first visible-light-enabled direct C3-H alkylation/arylation of quinoxalin-2(1H)-ones with unactivated alkyl/aryl chlorides under metal-free conditions. A wide range alkyl and aryl containing different functionalities are coupled a variety quinoxalin-2(1H)-one derivatives mild reaction conditions to afford C3-alkyl/aryl substituted in moderate good yields.

Язык: Английский

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Demystifying the recent photochemical and electrochemical tricks on installing the magic methyl group: A comprehensive overview

Green Chemistry, Год журнала: 2024, Номер 26(14), С. 8161 - 8203

Опубликована: Янв. 1, 2024

The strategic installation of the “magic methyl” group has become highly desirable for drug discovery. This review summarized recent photochemical and electrochemical strategies in installing methyl group.

Язык: Английский

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Photo‐Induced C−H Methylation Reactions

Chemistry - A European Journal, Год журнала: 2023, Номер 29(72)

Опубликована: Окт. 6, 2023

Direct C-H methylation is a highly valuable approach for introducing methyl groups into organic molecules, particularly in pharmaceutical chemistry. Among the various methodologies available, photo-induced stands out as an exceptional choice due to its mild reaction conditions, energy efficiency, and compatibility with functional groups. This article offers comprehensive review of photochemical strategies employed direct selective C(sp3 )-H, C(sp2 C(sp)-H bonds molecules. The discussed encompass transition-metal-based photocatalysis, organophotocatalysis, well other metal-free approaches, including electron donor-acceptor (EDA)-enabled transformations. Importantly, wide range easily accessible agents such tert-butyl peroxide, methanol, DMSO, ether, TsOMe, N-(acetoxy)phthalimide, acetic acid, halides, even methane can serve effective methylating reagents modifying diverse targets. These advancements are anticipated drive further progress fields synthesis, development, opening up exciting avenues creating novel molecules discovering new drug compounds.

Язык: Английский

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Photochemical Synthesis of 1,4‐Dicarbonyl Containing Quinoxalin‐2(1H)‐Ones through Consecutive Photoredox Catalysis

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1833 - 1839

Опубликована: Фев. 8, 2024

Abstract Herein, we report a photochemical synthesis of 1,4‐dicarbonyl containing quinoxalin‐2(1 H )‐ones through consecutive photoredox catalysed reactions. A wide range C3‐modified were obtained in 53–91% yields by this approach. Mechanistic studies including radical trapping, EPR studies, D‐labelling investigations, and many other control experiments well explained the proposed mechanism.

Язык: Английский

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EDA Complex from BCP‐Thianthrenium Salt: A Catalyst‐free Strategy To Access 1‐Trifluoromethyl‐3‐quinoxaline Derivatives Bicyclo[1.1.1]pentanes

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Май 13, 2024

Abstract The construction of bicyclo[1.1.1.]pentanes (BCPs) typically require the cumbersome use labile [1.1.1.]propellane in solution and involve multicomponent radical reactions, which commonly produce undesired by‐products that hinder efficient BCPs. In this paper, we present a catalyst‐free strategy by constructing an electron donor‐acceptor (EDA) complex utilizing naturally electron‐deficient nature BCP thianthrenium salt, were irradiated with visible light to obtain trifluoromethyl‐BCP radicals through SET process, subsequently reacted various substituted quinoxalines. Moreover, successful structural modification drug molecule derivatives confirm utility scheme field discovery.

Язык: Английский

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