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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Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2139 - 2144

Опубликована: Март 22, 2023

The three-component reactions of enaminones, α-diazo esters/ketones, and t-butyl nitrite (TBN) for the switchable synthesis isomeric isoxazoles have been realized. catalysis with Cu(II) salt provides 3,4-disubsituted via [3 + 2] cycloaddition. On other hand, Ag(I) identical substrates leads to reversed C3 C4 substitution based on a key [2 1]

Язык: Английский

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Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides

Organic Letters, Год журнала: 2023, Номер 25(40), С. 7298 - 7303

Опубликована: Окт. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Язык: Английский

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Three-component synthesis ofN-naphthyl pyrazolesviaRh(iii)-catalyzed cascade pyrazole annulation and Satoh–Miura benzannulation

Chemical Communications, Год журнала: 2023, Номер 59(27), С. 4036 - 4039

Опубликована: Янв. 1, 2023

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(III) catalysis. synthetic employing simple substrates lead to simultaneous construction dual cyclic moieties, including a pyrazole ring phenyl ring, sequential formation two C-N three C-C bonds.

Язык: Английский

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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7214 - 7219

Опубликована: Сен. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Язык: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

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Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4833 - 4838

Опубликована: Март 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Язык: Английский

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Язык: Английский

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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 homophthalimide spironaphthalenones through [5 + 1] spiroannulation of aryl/alkenyl enaminones with diazo homophthalimides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(17), С. 4282 - 4288

Опубликована: Янв. 1, 2023

Presented herein is a novel synthesis of homophthalimide spironaphthalenones from the cascade reaction enaminones with diazo homophthalimides.

Язык: Английский

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