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

---

Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(10)

Published: Sept. 13, 2023

Fused coumarins, because of their remarkable biological and therapeutic properties, particularly pyranocoumarins, have caught the interest synthetic organic chemists, leading to development more efficient environmentally friendly protocols for synthesizing pyranocoumarin derivatives. These compounds are most promising heterocycles discovered in both natural sources, with anti-inflammatory, anti-HIV, antitubercular, antihyperglycemic, antibacterial properties. This review employed scientific databases Scopus, Web Science, Google Scholar, PubMed up end 2022, as well combining terms synthesis, isolation, structural elucidation, activity. Among catalysts employed, acidic magnetic nanocatalysts, transition metal catalysts, carbon-based all demonstrated improved reaction yields facilitated reactions under milder conditions. Herein, present discusses various multicomponent strategies pyranocoumarins catalyzed by metal-based metal-free potential pharmacological activities.

Language: Английский

---

Precision Propargylic Substitution Reaction: Pd-Catalyzed Suzuki–Miyaura Coupling of Nonactivated Propargylamines with Boronic Acids

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

Published: Aug. 31, 2024

Palladium-catalyzed Suzuki–Miyaura cross-coupling is an efficient approach for C–C bond construction. Here we report a deaminative reaction to achieve chemo- and regioselectivity in the of nonactivated propargylamines with boronic acids, which methyl propiolate introduced promote cleavage C–N form bond. This method features wide range substrates, good functional group tolerance, ease operation, providing alternative accessing valuable propargylated aromatic compounds.

Language: Английский

---

Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of Indole-Benzofuran Bis-Heterocycles

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

Published: Nov. 22, 2024

A one-pot, three-component synthesis of indole-benzofuran bis-heterocycles from terminal alkynes, salicylaldehydes, and indoles has been developed via copper-catalyzed tandem annulation. This catalytic system utilizes readily available starting materials, enabling predictable with broad substrate versatility, excellent regiocontrol, gram-scale amenability. The reaction proceeds a sequential pathway involving A3 coupling, 1,4-conjugate addition, 5-exo-dig cyclization.

Language: Английский

---

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

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9159 - 9172

Published: Jan. 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.

Language: Английский

---

Exploitation of ninhydrin core towards spiropyranocoumarin and benzofuranyl coumarin: Synthesis, crystal structure and self-assembly

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1318, P. 139185 - 139185

Published: July 1, 2024

Language: Английский

---

Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 421 - 484

Published: Jan. 1, 2024

Language: Английский

---

Modular access to furo[3,2-c]chromen-4-ones via Yb(OTf)₃-catalyzed [3 + 2] annulation of 4-hydroxycoumarins with β-nitroalkenes

RSC Advances, Journal Year: 2024, Volume and Issue: 14(27), P. 19581 - 19585

Published: Jan. 1, 2024

We have developed a facile and efficient strategy for modular access to furo[3,2- c ]chromen-4-ones by formation of furan ring from readily available starting materials with broad functional group compatibility in single step.

Language: Английский

---