Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

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Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109683 - 109683

Published: March 2, 2024

Language: Английский

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Divergent Synthesis of 2-Chromonyl-3-hydrazono-chromones and 2-Alkoxy-3-hydrazono-chromones through Switchable Annulation Reactions of o-Hydroxyphenylenaminones with Aryldiazonium Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4980 - 4985

Published: June 4, 2024

An unprecedented selective chromone annulation reaction controlled by solvent for the divergent synthesis of two types 2,3-disubstituted skeletons has been developed. A variety 2-chromonyl-3-hydrazono-chromones and 2-alkoxy-3-hydrazono-chromones were constructed efficiently from readily available

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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I₂-DMSO mediated dual α,β-C(sp²)–H functionalization/bicyclization of o-hydroxyphenyl enaminones to construct C2,C3-disubstituted chromone derivatives: chromeno[2,3-b]pyrrol-4(1H)-ones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4843 - 4847

Published: Jan. 1, 2023

An unprecedented dual α,β-C(sp 2 )–H functionalization/bicyclization strategy of o -hydroxyphenyl enaminones for the preparation chromeno[2,3- b ]pyrrol-4(1 H )-ones has been established.

Language: Английский

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Spectroscopic elucidation, quantum chemical computations (FMO, HOMO–LUMO, MEP, NLO), and biological activity on some novel heterocyclic compounds using 3-substituted-6,8-dimethylchromones

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(18), P. 1523 - 1550

Published: Aug. 28, 2024

The chemical transformations of substituted chromones 1a–c were examined toward some nucleophiles namely dimedone (R1), 4-hydroxycoumarin (R2) and 4-hydroxy-1-methylquinolin-2(1H)-one (R3). DFT computation at the B3LYP/6-311 G(d,p) level theory was used to perform theoretical computations for produced compounds. HOMO LUMO analyses performed determine electronic charge distribution reactivity molecules. Molecular electrostatic potential (MEP) surface analysis utilized predict molecule's reactive sites. Moreover, studied compounds showed NLO characteristics, where they have first order hyperpolarizability greater than urea. In addition, GIAO method estimate 1H-NMR 13C-NMR shifts; findings compared with experimental values. Testing generated antibacterial anticancer activities revealed varied degrees inhibitory effect. According Lipinski, Veber, Egen rules, these exhibit physicochemical properties.

Language: Английский

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Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8632 - 8640

Published: June 6, 2024

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, preliminary experiments revealed that reaction probably proceeded cation instead radical pathway.

Language: Английский

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Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3670 - 3675

Published: July 2, 2024

Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as reaction partners o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists cascade iodination, chromone annulation, and Arbuzov‐type C−P cross coupling major transformations. In addition to providing enaminone‐based synthetic chromone‐3‐phosphonates, work shows advantage step economy skipping separate operation preparing iodo‐functionalized intermediate.

Language: Английский

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Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9236 - 9241

Published: Jan. 1, 2023

A convenient and efficient method for the synthesis of difluoro/trifluoromethyl carbinol-containing chromone derivatives has been developed.

Language: Английский

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Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 644 - 655

Published: Dec. 13, 2023

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using N-aminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, yields, regioselectivity. Preliminary mechanistic studies support radical property involvement N-centered intermediates.

Language: Английский

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