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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An overview on copper in industrial chemistry: From ancient pigment to modern catalysis

Coordination Chemistry Reviews, Год журнала: 2025, Номер 529, С. 216438 - 216438

Опубликована: Янв. 17, 2025

Язык: Английский

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Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Год журнала: 2024, Номер 11, С. 100082 - 100082

Опубликована: Июль 3, 2024

Язык: Английский

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Ag(i)-catalyzed asymmetric (2+4) annulation reaction of 5-alkenyl thiazolones: synthesis of enantioenriched spiro[cyclohexenamines-thiazolones]

Chemical Communications, Год журнала: 2024, Номер 60(68), С. 9062 - 9065

Опубликована: Янв. 1, 2024

We report the first metal-catalyzed (2+4) annulation of 5-alkenyl thiazolones and dicyanoalkylidenes, delivering spiro[cyclohexenamines-thiazolones] with high stereoselectivities.

Язык: Английский

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Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans

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

Опубликована: Янв. 30, 2025

A regioselective [3 + 2] annulation of β,γ-alkynyl-α-ketimino esters with 1,3-dicarbonyls is disclosed. series Z-selective dihydrofurans bearing an exocyclic double bond and a quaternary carbon center are accessed without the usage base. Control deuterium-labeling experiments have been investigated to probe into reaction mechanism. The catalyst base-free nucleophilic addition highlights transformation.

Язык: Английский

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Asymmetric Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 15, 2025

Herein, we disclose a novel organocatalytic approach for the enantioselective synthesis of 1,4-sulfur-bridged piperidinone skeletons via sequential aza-Michael/Michael/Mannich domino reaction 2-aminochalcones and 5-alkenyl-thiazolones. The one-pot catalyzed by bifunctional squaramide catalyst furnishes bridged polycyclic compounds with five contiguous stereocenters (three tertiary, two heteroquaternary) in excellent yields (up to 95%) stereochemical outcomes 99% ee up >20:1 dr). methodology offers outstanding control on regio- chemoselectivity, showcasing broad substrate compatibility. Additionally, is scalable postsynthetic transformation spirothiazolone-tetrahydroquinoline derivative further amplifies synthetic utility methodology.

Язык: Английский

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Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition: access to oxygen heterocycles featuring a CF₃-substituted quaternary stereocenter

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An enantioselective Cu( i )-catalyzed propargylic [3 + 2] cycloaddition reaction for the synthesis of optically active oxygen heterocycles bearing CF 3 -substituted quaternary stereocenters has been realized.

Язык: Английский

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Asymmetric Organocatalytic Diels–Alder Reaction of Olefinic Azlactones with Unsaturated Thiazolones: Access to Spirocyclohexenone Thiazolone Skeletons

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(20), С. 15271 - 15281

Опубликована: Окт. 10, 2024

Chiral bifunctional thiourea-catalyzed Diels-Alder reaction between olefinic azlactones and alkylidene thiazolone derivatives is reported here for the first time. The asymmetric delivers vicinal tertiary-quaternary stereocenters in spirocyclohexenone thiazolones moderate to high yields good stereochemical outcomes. protocol can be adapted a broad array of substrates. Moreover, scaled up, chiral was converted into valuable spirocyclic-1,2-amidoalcohol highlighting synthetic utility our methodology.

Язык: Английский

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Enantioselective Synthesis of Spirooxindole‐pyran and furan Scaffolds via Copper‐Catalyzed Formal (3+3) and (3+2) Cycloaddition of Isatin‐derived Propargylic Esters

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Дек. 12, 2024

Herein, we report a copper-catalyzed enantioselective formal (3+3) and (3+2) cycloaddition reaction of isatin-derived tertiary propargylic esters with N,N-dimethylbarbituric acid 4-hydroxycoumarins, respectively. In this process, the ester serves as both C3- C2-synthons, facilitating synthesis optically active spirooxindole-pyran furan scaffolds featuring an all-carbon quaternary stereocenter. The delivers these spirocyclic frameworks in good yields high enantioselectivities. Additionally, scalability reactions transformation chiral intermediates into valuable structures emphasize synthetic practical importance strategy.

Язык: Английский

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Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(46), С. 9159 - 9172

Опубликована: Янв. 1, 2023

Facile access to furan fused heterocyclic scaffolds through a regioselective cascade reaction of propargylamines with 4-hydroxy-2H-pyran-2-ones and 4-hydroxy-6-methylpyridin-2(1H)-one has been achieved. This presumably involves the formation ortho-alkynyl quinone methide (o-AQM), 1,4-conjugate addition, followed by 5-exo-dig annulation, 1,3-H shift process. Moreover, provides new efficient method for synthesis highly sterically congested 3-phenolic furo[3,2-c]pyran-4-ones furo[3,2-c]pyridin-4(5H)-ones ring from readily available starting materials in good high yields (50-82%) broad functional group compatibility single step. Significantly, strategy described here is easily scalable several useful synthetic transformations prepared arene-functionalized 4H-furo[3,2-c]pyran-4-ones were also performed.

Язык: Английский

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