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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Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones

Organic Letters, Год журнала: 2024, Номер 26(4), С. 786 - 791

Опубликована: Янв. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

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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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

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

Опубликована: Янв. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Язык: Английский

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Rh(ii)-catalysed N²-selective arylation of benzotriazoles and indazoles using quinoid carbenes via 1,5-H shift

Chemical Communications, Год журнала: 2024, Номер 60(35), С. 4727 - 4730

Опубликована: Янв. 1, 2024

An efficient Rh( ii )-catalyzed N 2 -selective arylation of benzotriazole and indazole is developed using diazonaphthoquinone. The reaction proceeds via nucleophilic addition the (of 1 H tautomer) center to quinoid-carbene followed by a 1,5-H shift.

Язык: Английский

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Directed Cascade C–H Functionalization/2-Fold Annulation with Vinylcyclopropanes: Access to Tetrahydrobenzo[g]isochromen-10-ones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 20, 2025

Rh-catalyzed enaminone directed cascade C-H functionalization/2-fold annulation with vinylcyclopropanes has been accomplished to afford functionalized tetrahydrobenzo[g]isochromen-10-ones. The sequential C-H/C-C functionalization, C-C/C-O bond formation, redox-neutral conditions, functional group tolerance, and late-stage modification of the natural products are important practical features.

Язык: Английский

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Synthesis of 3‐Hydroxyfluorenones Based on the Cascade Reaction of Aryl Enaminones with Benzyl Substituted Cyclopropanols

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

Comprehensive Summary Presented herein is a novel synthesis of 3‐hydroxyfluorenones through the cascade reaction aryl enaminones with benzyl substituted cyclopropanols. The formation product initiated by introduction an enone moiety onto enaminone cyclopropanol as homoenolate precursor C−H bond activation, followed intramolecular enamine Michael addition, enol amine elimination and aromatization‐driven oxidative dehydrogenation. To our knowledge, this should be first example for specific 3‐hydroxyfluorenone derivatives via simultaneous both indenone phenol scaffolds C−H/C−C/C−N activation three C−C formation. In general, newly developed protocol features easily accessible substrates, synthetically pharmaceutically valuable products, unique pathway, good compatibility various functional groups ready scalability.

Язык: Английский

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Divergent Synthesis of Naphthalenone Spiroindanediones or 4‐Acyl‐1‐naphthols from Aryl Enaminones Featuring Reuse of Dimethylamine

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(15), С. 3372 - 3378

Опубликована: Май 29, 2024

Abstract Presented herein is a switchable synthesis of naphthalenone spiroindanediones or 4‐acyl‐1‐naphthols via condition‐controlled divergent cascade reactions aryl enaminones with diazoindanediones. When the reaction was carried out in presence an oxidative additive, spiroindanedione formed through C( sp 2 )−H alkylation followed by simultaneous spiroannulation and elimination dimethylamine. acid on other hand, 4‐acyl‐1‐naphthol ring opening moiety attacked situ released In addition, are suitable for gram‐scale applications compatible variety substrates. Moreover, naphthol products allow structural elaborations hybridization drug, thus further enhancing value this developed method.

Язык: Английский

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Direct Aromatic Nitrosation Using 2-Methoxyethyl Nitrite as a NO Cation Source

Organic Letters, Год журнала: 2024, Номер 26(26), С. 5517 - 5521

Опубликована: Июнь 26, 2024

This work presents an acid-free method for aromatic nitrosation using 2-methoxyethyl nitrite (MOE-ONO). While originally developed as a NO

Язык: Английский

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Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C–H Activation for the Synthesis of Fluorenones

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 19, 2024

An efficient method for construction of various fluorenones has been achieved via Rh(III)-catalyzed C–H activation/[4 + 2] annulation/aromatization sequences simple and readily available enaminones 1,3-dienes. This protocol showed good substrate compatibility as an array structurally electronically diverse prepared efficiently in moderate to yields preparative scale utility showing very efficiency the late-stage functionalization complex valuable molecules.

Язык: Английский

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