Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Feb. 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).

Language: Английский

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Tertiary‐Amine Controlled (3+3) or (4+2) Annulations of β′‐Acetoxy Allenoates with N‐Sulfonyl Ketimines: An Entry to m‐Teraryl and Fused Dihydropyridines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1165 - 1175

Published: Jan. 10, 2024

Abstract Lewis base dependent (3+3) and (4+2) annulations of β′ ‐acetoxy allenoates with N ‐sulfonyl ketimines offer m ‐teraryl fused dihydropyridines varying substituents depending on the tertiary amine as well subtle changes in reaction conditions. The triazabicyclodecene (TBD)‐catalyzed annulation involves 1,2‐elimination followed by 6‐ endo ‐dig cyclization key steps delivering 1,4‐hydropyridines. same reactants under DMAP catalysis via Mannich coupling, rather than C−N bond cleavage/aromatization. Key intermediates have been identified HRMS studies.

Language: Английский

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Acetoxy allenoates as emerging synthons in annulation/cycloaddition reactions

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The emergence of acetoxy allenoates as versatile synthons to generate a plethora annulation/cycloaddition products via electrophilic diene–phosphonium/ammonium intermediates is highlighted in this feature article.

Language: Английский

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Metal-free three-component reactions of alkynes for the construction of 3,4-difunctionalized benzo[h]coumarins

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel approach for constructing 3,4-difunctionalized benzo[ h ]coumarins through a metal-free multicomponent reactions with mild reaction conditions.

Language: Английский

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Synthesis of Isoxazol-5(2H)-one Derivatives via (^tBuO)₂Mg Promoted [3 + 2] Annulations of δ-Acetoxy Allenoates with Hydroxylamine

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8291 - 8298

Published: May 28, 2024

Herein, an efficient (

Language: Английский

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Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10816 - 10830

Published: July 15, 2024

Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β'-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed gives benzothiazole-fused 1,4-dihydropyridine carboxylates (3 + 3) chemoselectively. By contrast, PR

Language: Английский

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Synthesis of π-Extended Coumarins Using δ-Acetoxy Allenoate as a 5C-Synthon

Synfacts, Journal Year: 2023, Volume and Issue: 19(11), P. 1159 - 1159

Published: Oct. 14, 2023

Language: Английский

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Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 31, 2024

Abstract Cyclic N ‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities these four different isocyanide‐based multicomponent reactions. Our goal was to create libraries compounds functional groups vectors that are compatible for structural elaboration optimization their physical properties. We synthesized 15 unprecedented high diversity complexity, whereas have obtained single crystal structures each scaffold, unraveling geometrical features potential employment drug discovery.

Language: Английский

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Annulation Reactions of Isoquinolinium Ylides with Sulfamate-Derived Cyclic Imines toward Polycyclic 1,3-Benzoxazepine Heterocycles

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: June 20, 2024

Abstract A dearomatization-guided and (3+2) cycloaddition-triggered annulation reaction of in situ formed isoquinolinium ylides with sulfamate-derived cyclic imines is reported, offering a cogent synthesis tetracyclic 1,3-benzoxazepine frameworks high yields. The protocol features successive ring-forming ring-breaking events cascade fashion also scalable.

Language: Английский

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Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

A versatile and atom-economic three-component reaction between 3-cyano-4-styrylcoumarins, 1,3-indandione, aliphatic alcohols is described for synthesizing diversely multifunctionalized benzocoumarins. This strategy allows facile access to various benzocoumarins bearing an amine a substituted benzoyl scaffold under simple heating conditions. Readily available precursors, operational simplicity, acceptable functional group tolerance, excellent yields are some highlighted advantages of this transformation.

Language: Английский

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