Rh-Catalyzed and Self-Directed Aromatic C–H Activation of Enaminones to Divergent Alkenylated and Annulated Compounds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 27, 2025

By means of simple Rh catalysis, the direct activation ortho-C-H bond in aryl enaminones has been realized with enaminone structure as a traceless directing fragment. The products resulting from C-H alkenylation and further annulation via intramolecular addition could be accessed depending upon alkenes. annulated used for easy synthesis valuable 2-aza-fluorenones one-pot operation by employing NH4OAc.

Язык: Английский

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Synthesis of Multisubstituted Arylnitriles via Tf₂O-Mediated Benzannulation of Enaminones with Acylacetonitriles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

A novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 1] benzannulation enaminones acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation aromatization. Additionally, trifluoromethanesulfonate 6 identified as crucial intermediate in this process.

Язык: 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, Год журнала: 2024, Номер 366(17), С. 3670 - 3675

Опубликована: Июль 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.

Язык: Английский

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An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110784 - 110784

Опубликована: Дек. 1, 2024

Язык: Английский

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Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134494 - 134494

Опубликована: Янв. 1, 2025

Язык: Английский

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Ring opening and recyclization reactions with 3-functionalized chromones: Recent synthetic approaches for five, six and seven membered heterocycles

Synthetic Communications, Год журнала: 2025, Номер unknown, С. 1 - 24

Опубликована: Фев. 12, 2025

Язык: Английский

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Eco-Friendly and Efficient Synthesis of 2-Hydroxy-3-Hydrazono-Chromones Through α,β-C(sp2)–H Bond Difunctionalization/Chromone Annulation Reaction of o-Hydroxyaryl Enaminones, Water, and Aryldiazonium Salts

Molecules, Год журнала: 2025, Номер 30(6), С. 1194 - 1194

Опубликована: Март 7, 2025

A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), aryldiazonium salts has been developed under mild reaction conditions. This α,β-C(sp2)–H bond difunctionalization/chromone annulation strategy is achieved by building two C(sp3)–O bonds a C(sp2)-N bond, which provides practical pathway the preparation of 2-hydroxy-3-hydrazono-chromones in moderate to excellent yields, enabling broad substrate scope good functional group tolerance, as well gram-scale synthesis. protocol offers valuable tool synthesizing diverse functionalized chromones with potential applications drug discovery industrial

Язык: Английский

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Electrochemical Annulation of p-Alkoxy or p-Hydroxy Anilines with Enaminones for Selective Indole and Benzofuran Synthesis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

The green and sustainable electrochemical oxidative cyclization of enaminones with p-methoxy/p-hydroxy anilines has been developed, enabling the regioselective synthesis indoles benzofurans. methods are significant advantage not only due to mild metal-free conditions, but also because employment easily available stable aniline substrates replace unstable quinoneimide for a similar annulation in previous work.

Язык: Английский

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Domino Approach to Heterocycles-Based Unsymmetrical Triarylmethanes through Heteroannulation of 2-(2-Enynyl)-pyridines with Enaminones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12104 - 12117

Опубликована: Авг. 13, 2024

Herein, we report a copper-catalyzed protocol to access unsymmetrical triarylmethanes containing both indolizine and the chromone scaffolds in same molecule via 5-endo-dig cyclization of 2-(2-enynyl)-pyridines followed by reaction with 2-hydroxyaryl enaminones. A variety enaminones were subjected under optimal conditions, respective obtained good excellent yields.

Язык: Английский

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General access to furan-substituted gem-difluoroalkenes enabled by PFTB-promoted cross-coupling of ene-yne-ketones and difluorocarbene

Chemical Science, Год журнала: 2024, Номер 16(3), С. 1455 - 1464

Опубликована: Дек. 23, 2024

An efficient method for the tandem cyclization cross-coupling of conjugated ene-yne-ketones with difluorocarbene via PFTB promotion is described, providing facile access to diverse furan-substituted difluoroalkenes potential antitumor potency.

Язык: Английский

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