Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF₃-ynones via C–H/N–H/C–N/C–C bond cleavage

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 1917 - 1923

Опубликована: Янв. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Язык: Английский

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Synthesis of 1,7-Fused Indolines Tethered with Spiroindolinone Based on C–H Activation Strategy with Air as a Sustainable Oxidant

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1880 - 1897

Опубликована: Янв. 22, 2024

Herein, we present an efficient synthesis of 1,7-fused indolines tethered with a spiroindolinonyl moiety through the cascade reaction indolin-1-yl(aryl)methanimines diazo oxindoles. To best our knowledge, this is first example in which indoline skeleton was constructed along simultaneous introduction spiro element initiated by C–H bond activation indoline. In forming title product, substrate and coupling partner demonstrated unprecedented pattern latter acts as C1 synthon to participate construction spirocyclic scaffold reductive elimination key seven-membered Ru(II) species using air effective sustainable oxidant regenerate active catalyst. Moreover, studies on cytotoxicity selected products against several human cancer cell lines their potential lead compounds for development anticancer drugs. With notable features such simple economical substrates, pharmaceutically valuable sophisticated skeleton, mild conditions, cost-free oxidants, high efficiency, excellent compatibility diverse functional groups, scalability, method expected find wide applications related areas.

Язык: Английский

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Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10180 - 10196

Опубликована: Июль 4, 2024

Presented herein are novel syntheses of CF

Язык: Английский

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Synthesis of CF₃-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7828 - 7842

Опубликована: Май 22, 2024

Presented herein is a novel synthesis of CF

Язык: Английский

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Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles

Chemical Communications, Год журнала: 2024, Номер 60(51), С. 6536 - 6539

Опубликована: Янв. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

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 O-Heterocycle Spiro-Fused Cyclopentaquinolinones and Cyclopentaindenes through Visible Light-Induced Radical Cyclization Reactions

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12641 - 12657

Опубликована: Авг. 17, 2023

Presented herein is an effective and sustainable synthesis of O-heterocycle spiro-fused cyclopentaquinolinone cyclopentaindene derivatives through light-driven cascade reactions N-(o-ethynylaryl)acrylamides or 2-(2-(phenylethynyl)benzyl)acrylate with various O-heterocycles. Experimental mechanistic studies revealed that these are initiated by visible light-induced radical formation from its regioselective addition onto the acrylamide acrylate moiety followed 6-exo-dig 5-endo-trig annulation, which terminated single electron oxidation proton elimination. Compared previously reported synthetic methods for similar purposes, this newly developed protocol has advantages such as a broad substrate scope, extremely mild reaction conditions, excellent atom-economy, high efficiency, good compatibility diverse functional groups. With all merits, method expected to find wide applications in related research arena.

Язык: Английский

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Synthesis of CF3-Indazoles via Rh(III)-Catalyzed C-H [4+1] Annulation of Azobenzenes with CF3-Imidoyl Sulfoxonium Ylides

Molecules, Год журнала: 2025, Номер 30(1), С. 183 - 183

Опубликована: Янв. 5, 2025

An efficient Rh(III)-catalyzed C-H activation of azobenzenes and subsequent [4+1] cascade annulation with CF3-imidoyl sulfoxonium ylides was developed, yielding diverse CF3-indazoles. This protocol featured easily available starting materials, excellent functional group tolerance high efficiency. Moreover, the antitumor activities selected CF3-indazoles against human cancer cell lines were also studied, results indicated that several compounds displayed considerable antiproliferative activities.

Язык: Английский

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Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF₃-Imidoyl Sulfoxonium Ylides via Triple C–H Activation

Organic Letters, Год журнала: 2025, Номер 27(2), С. 657 - 662

Опубликована: Янв. 7, 2025

A condition-controlled Rh(III)-catalyzed selective synthesis of CF3-substituted indoles and pyrido[2,1-a]isoindoles from 2-arylpyridines CF3-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)3(SbF6)2/HFIP system afforded via triple C–H activation, while the [Cp*RhCl2]2/MeCN condition selectively furnished through [4 + 1] annulation. notable advantages this developed method included readily available starting materials, broad substrate scope, excellent chemoselectivity. Importantly, several selected products showed promising antitumor activities.

Язык: Английский

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Synthesis of Polyfunctional Indazoles via Novel Rearrangement of Isatin Derivatives

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

Опубликована: Фев. 3, 2025

Abstract In this work we present a new method for indazole synthesis through the unexpected rearrangement of various 7‐nitroisatins during reaction with hydrazine hydrate. The pyrazole cycle is formed via direct metal‐free C−H amination. We demonstrate limitations discovered approach and several accessible methods functionalization compounds to obtain novel derivatives.

Язык: Английский

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