Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7425 - 7430

Опубликована: Авг. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Язык: Английский

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Synthesis of Indenone-Fused Pyran Derivatives from Aryl Enaminones and Cyclopropenones through Unsymmetrical Relay C–H Bond Activation and Double C–C/C–O Bond Formation

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6602 - 6607

Опубликована: Июль 30, 2024

Presented herein is a novel synthesis of indenone-fused pyran derivatives via the cascade reactions aryl enaminones with cyclopropenones. The formation products involves one-pot procedure consisting C–H bond and enamine functionalization along C–C cleavage cyclopropenone 1,3-rearrangement in situ-formed allylic alcohol moiety followed by intramolecular O-nucleophilic addition Me2NH elimination. To our knowledge, this first simultaneous both indenone scaffolds through concurrent unsymmetrical relay activation double C–C/C–O formation. Moreover, usefulness method further showcased its suitability for large-scale synthetic scenarios diverse transformations products.

Язык: Английский

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Synthesis of CF₃-Azafluorenes through the Cascade Reaction of 2H-Imidazoles with CF₃-Ynones

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 25, 2024

A concise synthesis of trifluoromethyl (CF

Язык: Английский

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Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 694 - 694

Опубликована: Янв. 1, 2025

Язык: Английский

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Ring-Opening Cyclization (ROC) of spiro-Epoxyoxindoles with Indoles/Aldehydes: An Easy Access to Polyheterocyclic spiro-Oxindoles

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

A simple one-pot, two-step strategy for the synthesis of three-dimensional (3D) polyheterocyclic spiro-oxindoles by Lewis-acid-catalyzed Friedel–Crafts type C-3 alkylation indoles via regioselective nucleophilic ring opening spiro-epoxyoxindoles, followed p-TSA-catalyzed Pictet-Spengler reaction with aldehydes in up to 98% yield and 1.4:1 diastereomeric ratio has been developed.

Язык: Английский

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Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Язык: Английский

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Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues

ACS Organic & Inorganic Au, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

Язык: Английский

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Photoredox-Catalyzed Carbamoyl Radical-Initiated Dearomative Spirocyclization To Access Spiro-Cyclohexadiene Oxindoles

Organic Letters, Год журнала: 2024, Номер 26(40), С. 8503 - 8508

Опубликована: Окт. 1, 2024

The sustainable construction of spirocyclic compounds is important to the scientific community and pharmaceutical industries. Herein, we demonstrate a carbamoyl radical-initiated intramolecular dearomative spirocyclization access spiro-cyclohexadiene oxindoles under visible light irradiation, which constitutes first example accessing I-substituted derivatives that facilitate diversified transformations. Additionally, scalability, late-stage modification drugs, significant antitumor activity products novel synthesis platform for expediting drug development.

Язык: Английский

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Recent Advances in the Synthetic Applications of Nitrosoarene Chemistry

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

This review covers reactions involving nitrosoarenes over the last decade, including cyclization, with attacks at oxygen or nitrogen terminus, dimerization, rearrangement, coordination, and other significant reactions.

Язык: Английский

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Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides

Organic Letters, Год журнала: 2024, Номер 26(50), С. 10951 - 10957

Опубликована: Дек. 10, 2024

Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly multisubstituted aminoisoquinolines, class heterocycles that play privileged role in organic synthesis pharmaceutical development. This new catalytic process exhibits programmability, including directed C–H acetylation, nucleophilic cyclization, alcoholysis. Remarkably, various 2-arylquinazolinones could be employed excellent yields broad functional group tolerance. heterocycle-to-heterocycle protocol is compatible green chemistry using an EtOH solvent releasing H2O dimethyl sulfoxide as byproducts.

Язык: Английский

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