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, Год журнала: 2024, Номер 26(23), С. 4980 - 4985

Опубликована: Июнь 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

Язык: Английский

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Controllable Synthesis of N-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5 + 1] and [5 + 2] Cyclizations

Organic Letters, Год журнала: 2023, Номер 26(1), С. 332 - 337

Опубликована: Дек. 28, 2023

The Brønsted acid-controlled switchable synthesis of indoline-fused tetrahydroquinolines and indole-fused benzazepines was developed through hydride transfer-enabled formal [5 + 1] 2] cyclization reactions from indoles N-alkyl o-aminobenzoketones. Indoline, furanone, tetrahydroquinoline hybridized pentacyclic products were unprecedentedly accessed via a cascade condensation/hydride transfer/dearomatization-cyclization/deethylation/nucleophilic addition process. In addition, the undeveloped transfer-involved cyclizations also realized for direct construction benzazepines.

Язык: Английский

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Pd-Catalyzed Coupling of Aryl Chloride, Isocyanides, and Thiocarboxylate To Synthesize Thioamides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Although aryl chlorides are among the most abundant and stable aromatic electrophiles, coupling of with isocyanides has remained an unsolved challenge. Herein, we report a general transformation chlorides, isocyanides, thiocarboxylates to synthesize thioamides. The sterically hindered electron-rich Josiphos ligand significantly facilitates rate-determining oxidative addition step reduces toxicity toward metal center. combination thiocarboxylate as nucleophile ligands enabled coupling-tolerated various 1°, 2°, 3° which provides rapid, efficient, versatile method for synthesis large quantities thioamides, including those pharmaceutical relevance.

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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Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4262 - 4267

Опубликована: Май 9, 2024

A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process C–C bond activation and intermolecular allylic substitution was well-organized. The key transformation is in situ generated hydrolysis product cyclopropenone, which triggered new with vinylethylene carbonates. mechanism investigated, demonstrating high stereoselectivity excellent atomic economy process.

Язык: Английский

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Ag-Catalyzed Selective C–C Bond Activation of Cyclopropenones to Access α-Alkylidene Lactones

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6120 - 6124

Опубликована: Июль 11, 2024

A novel Ag-catalyzed ring opening of unsymmetric cyclopropenones for the stereoselective synthesis a diverse range α-alkylidene lactones has been developed. In this protocol, two different C-C(O) bonds were distinguished, demonstrating selective C-C bond activation. This reaction features wide substrate scope, good functional group compatibility, and high atom economy, providing versatile general approach to construction lactones.

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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Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 1331 - 1335

Опубликована: Янв. 3, 2024

A mild and concise method for the synthesis of chromenopyrrole from 2′-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on C═C bond 1,3-dipolarophile, generated in situ by ethyl isocyanoacetate AgOAc. This then followed intramolecular C–O formation with −OH group C5–H pyrrole, leading to chromenopyrroles.

Язык: Английский

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Dearomative spiroannulation of indoles enabled by the diaza-[1,2]-Wittig rearrangement

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(6), С. 1685 - 1691

Опубликована: Янв. 1, 2024

Reported herein is the first diaza-[1,2]-Wittig rearrangement-enabled dearomative spiroannulation reaction of indoles. This protocol features metal-free conditions, a redox-neutral process, broad substrate scope, and good yield.

Язык: Английский

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De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis

Advanced Science, Год журнала: 2024, Номер unknown

Опубликована: Июль 10, 2024

Precisely controlling the product selectivity of a reaction is an important objective in organic synthesis. α-Ketoamides are vital intermediates chemical transformations and privileged motifs numerous drugs, natural products, biologically active molecules. The selective synthesis α-ketoamides from feedstock chemicals safe operationally simple manner under mild conditions long-standing catalysis challenge. Herein, unprecedented TBD-switched Pd-catalyzed double isocyanide insertion for assembling ketoamides aqueous DMSO (hetero)aryl halides pseudohalides reported. effectiveness utility this protocol demonstrated by its diverse substrate scope (93 examples), ability to late-stage modify pharmaceuticals, scalability large-scale synthesis, pharmaceutically Mechanistic studies indicate that TBD key ligand modulates process, thereby selectively providing desired unique manner. In addition, imidoylpalladium(II) complex α-ketoimine amide successfully isolated determined X-ray analysis, confirming they probable catalytic pathway.

Язык: Английский

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