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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Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1679 - 1685

Published: March 15, 2024

Comprehensive Summary A novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 + OTf − ) for trifluoromethylation imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis TT–CF without requirement external oxidants or catalysts, aligning with principles green chemistry. wide range including imidazo[1,2‐ a ]pyridines benzo[ d ]imidazo[2,1‐ b ]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility various functional groups broad substrate scope. Moreover, method's applicability one‐pot sequential reactions enables reduction waste resource consumption by eliminating need intermediate purification steps.

Language: Английский

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Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 954 - 1014

Published: Dec. 14, 2023

The review summarises various photo- and electrochemical strategies for trifluoromethylation fluoroalkylation of different C(sp 3 )–H, 2 C(sp)–H bonds in several classes organic molecules.

Language: Английский

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Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(83), P. 12495 - 12498

Published: Jan. 1, 2023

CF3-substituted imidoyl sulfoxonium ylides (TFISYs) are extraordinarily versatile and powerful synthons for use in cyclization chemistry that affords diverse N-heterocycles. We first reacted TFISYs as a two-atom synthon with readily available azoalkenes then subjected the products to metal-free formal (4+2) cycloaddition chemistry. This protocol features mild conditions broad substrate scope, is simple operate, provides highly functionalized trifluoromethylpyridazines widely found bioactive molecules.

Language: Английский

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3-Perfluoroalkylated fluorescent coumarin dyes: rational molecular design and photophysical properties

Molecular Systems Design & Engineering, Journal Year: 2024, Volume and Issue: 9(4), P. 332 - 344

Published: Jan. 1, 2024

The photochemical properties of a coumarin derivative with promising electron-withdrawing fluoroalkyl group at the 3-position in solution and crystal were investigated detail.

Language: Английский

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Electrochemical trifluoroalkylation/annulation for the synthesis of CF₃-functionalized tetrahydroquinolines and dihydroquinolinones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8579 - 8583

Published: Jan. 1, 2023

Tuning the electronic structure of protecting groups on nitrogen atom substrates has emerged as an effective strategy to achieve tandem trifluoromethylation/C(sp2)-H annulation using Langlois' reagent CF3 source for electrochemical synthesis functionalized tetrahydroquinolines and dihydroquinolinones.

Language: Английский

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Polar-Effect-Directed Control in Site-Selectivity of Radical Substitution Enables C–H Perfluoroalkylation of Coumarins

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

Published: Sept. 26, 2024

A novel Ru-catalyzed protocol for C-7 selective C-H trifluoromethylation of coumarins in the presence light is presented. This reaction undergoes a radical type nucleophilic substitution instead electrophilic owing to benzocore activation as result lowering lowest unoccupied molecular orbital (LUMO).

Language: Английский

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