Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Фев. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Язык: Английский

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Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines

Organic Letters, Год журнала: 2024, Номер 26(1), С. 62 - 67

Опубликована: Янв. 3, 2024

We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.

Язык: Английский

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Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization

Organic Letters, Год журнала: 2024, Номер 26(24), С. 5136 - 5140

Опубликована: Июнь 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Язык: Английский

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Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1863 - 1876

Опубликована: Фев. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Язык: Английский

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Coumarin-Fused Nitrogenous Heterocycles: An Exploration of Annulation Strategies

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Март 21, 2025

Abstract Driven by advances in the pharmaceutical industry and materials science, search for innovative strategies synthesis functionalization of coumarin-fused nitrogenous heterocycles has intensified. These compounds, which combine bioactive coumarin core with various nitrogen-containing heterocycles, are significant interest due to their diverse biological activities promising potential applications. Traditional methods synthesizing these hybrid structures often encounter challenges such as low yields, limited functional group compatibility rigorous reaction conditions. To address challenges, there is a growing need development advanced synthetic that can effectively efficaciously produce aforementioned heterocyclic scaffolds. Towards this goal, annulation (e.g., cyclization, condensation, multicomponent reactions, transition-metal-catalyzed etc.) represent pivotal techniques construct evade constraints conventional approaches. In account, we highlight our recent progress on construction complex scaffolds order pave way further developments dynamic field. 1 Introduction 2 Exploring Acid-Catalyzed Annulation Strategies 3 Based C–H Activation 4 Oxidative 5 Conclusion

Язык: Английский

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Iridium(III)-Catalyzed Cyclization of Oximes with Iodonium Ylides: Synthesis of Multisubstituted Heterocyclic N-Oxides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Iridium(III)-catalyzed regioselective cyclization of substituted oximes with iodonium ylides has been described. This methodology offered multisubstituted heterocyclic N-oxides under mild reaction conditions in a redox-neutral manner. The was also compatible vinyl oximes. Additionally, substrate diversification carried out to illustrate the synthetic application protocol. A possible mechanism involving C-H bond activation proposed as well supported by isolation key five-membered iridacycle intermediate.

Язык: Английский

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Transition-Metal-Catalyzed Directed C–H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years

Molecules, Год журнала: 2024, Номер 29(15), С. 3567 - 3567

Опубликована: Июль 29, 2024

Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal migratory insertion processes. Among precursors, iodonium ylides serve as novel emerging precursor features including easy accessibility, thermal stability high activity, which have attracted great attention from organic chemists achieved tremendous success in transformation. In this review, recent progress on the application multifunctional coupling characteristics bond activation reactions is summarized, potential discussed.

Язык: Английский

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Cascade [4 + 1] Annulation through Activation of the C(sp²)–H Bond Enabling Benzothiadiazinoisoindolcarboxylate, Benzothiadiazinoisoindole, and Benzothiadiazinoisoindolepyrrolidinedione as Hybrid Spiro-Heterocyclic Frameworks

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7705 - 7717

Опубликована: Май 17, 2024

Two structurally distinct and biologically privileged succinimide isoindole heteroarenes bearing benzothiadiazinedioxide motif-centered hybrid conjugates are proficiently achieved through Rh(III)-catalyzed sequential C(sp

Язык: Английский

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Pragmatic Access to Hybrid Quinoxaline Scaffold Mediated by Elemental Sulfur Enabling Actualization to π-Extended and Aza-Annulated Heterocyclic Units

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 27, 2024

A metal-free approach for synthesizing hybrid quinoxaline derivatives from sulfoxonium ylide and a 1,5-bis-nucleophilic N-heterocycle mediated by elemental sulfur is presented to illuminate the [5+1] cascade cyclization sequence. Large-scale synthesis postsynthetic functionalizations annulative π-extension intramolecular aza-annulation reactions reveal potential utility actualize fabricated approach.

Язык: Английский

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Recent advances on the synthesis of pyrido[3,4-c]coumarin derivatives as the backbone of natural product schumanniophytin scaffolds

Monatshefte für Chemie - Chemical Monthly, Год журнала: 2024, Номер 155(11), С. 997 - 1026

Опубликована: Окт. 6, 2024

Язык: Английский

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