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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Recent advances in transition-metal-free C–H functionalization of imidazo[1,2-a]pyridines

Green Synthesis and Catalysis, Год журнала: 2022, Номер 3(3), С. 227 - 242

Опубликована: Март 19, 2022

Imidazo[1,2-a]pyridines are unique nitrogen-containing organic compounds with wide applications in pharmaceuticals, natural products, material science and organometallics. Due to their significant biological synthetic value, the construction of imidazo[1,2-a]pyridine scaffolds has been a highly intriguing research topic, substantial progress had made past decades. In this review, we aim summarize current advances direct C–H functionalization imidazo[1,2-a]pyridines under transition-metal-free conditions. For selected examples, focused on design catalytic cycle mechanism, as well representative outcomes applications.

Язык: Английский

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Dual-state emissive imidazo[1,2-α]pyridines with full color emission, acidochromism, viscosity-dependent fluorescence, and bioimaging applications

Dyes and Pigments, Год журнала: 2024, Номер 224, С. 112004 - 112004

Опубликована: Фев. 2, 2024

Язык: Английский

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Synthesis and site selective C–H functionalization of imidazo-[1,2-a]pyridines

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(36), С. 7267 - 7289

Опубликована: Янв. 1, 2023

Herein we disclose the synthesis and an overview of all functionalization reactions at each carbon atom, viz , C2, C3, C5, C6, C7 C8 imidazo[1,2- a ]pyridine.

Язык: Английский

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Solvent-Switched Manganese(I)-Catalyzed Regiodivergent Distal vs Proximal C–H Alkylation of Imidazopyridine with Maleimide

Organic Letters, Год журнала: 2021, Номер 23(19), С. 7370 - 7375

Опубликована: Сен. 20, 2021

A sustainable Mn(I)-catalyzed exclusive solvent-dependent functionalization of imidazopyridine with maleimide via an electrophilic metalation at the distal (in 2,2,2-trifluoroethanol (TFE)) and chelation assisted proximal tetrahydrofuran (THF)) has been developed. The strategy was successfully applied to drug Zolimidine a broad range substrates, thereby reflecting method's versatility.

Язык: Английский

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Looking deep into C–H functionalization: the synthesis and application of cyclopentadienyl and related metal catalysts

Chemical Communications, Год журнала: 2022, Номер 58(19), С. 3101 - 3121

Опубликована: Янв. 1, 2022

This feature review is focused on recent key applications of commonly used transition-metal Cp-type catalysts for C–H bond functionalizations.

Язык: Английский

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Catalyst-Controlled Chemodivergent Reactivity of Vinyl Cyclopropanes: A Selective Approach toward Indoles and Aniline Derivatives

Organic Letters, Год журнала: 2022, Номер 24(49), С. 9043 - 9048

Опубликована: Дек. 5, 2022

Herein, we disclose a catalyst-controlled chemodivergent approach to access C2-substituted indoles and diverse aniline derivatives with good chemo- stereoselectivity by employing vinylcyclopropanes (VCPs) as coupling partners via tandem C-H/C-C activation/annulation strategy. The key feature of this work is the divergent reactivity profile showcased VCPs, going beyond allylation under high-valent Rh-/MPAA catalyst system.

Язык: Английский

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A divergent construction of fused and bridged carbo-/heterocyclic scaffoldsviacascade reactions of aryl azomethine imines with vinyl cyclic carbonates

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(4), С. 1015 - 1021

Опубликована: Янв. 1, 2023

Presented herein is a divergent synthesis of indene-fused pyrazoles and bridged benzodiazepines tethered with hydroxymethyl group through the cascade reactions aryl azomethine imines vinyl cyclic carbonates.

Язык: Английский

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Palladium-Catalyzed Regioselective C3-Allylic Alkylation of 2-Aryl Imidazopyridines with MBH Carbonates

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2655 - 2665

Опубликована: Янв. 31, 2023

Imidazopyridine is an important framework that constitutes several pharmaceutical drugs and biologically active molecules. Herein, we present the palladium-catalyzed regioselective C3-allylic alkylation of 2-aryl imidazopyridines with MBH carbonates. This strategy furnishes a broad spectrum C3-allylated imidazopyridines, their structures have been unequivocally established using X-ray analysis. Besides, reaction can be easily scaled up on gram scale, ensuing product smoothly manipulated into synthetically useful entities.

Язык: Английский

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Unlocking Regiodivergence in Pd^II- and Rh^III-Mediated Site-Selective C–H Bond Alkynylation of Imidazopyridines

Organic Letters, Год журнала: 2023, Номер 25(9), С. 1447 - 1452

Опубликована: Фев. 24, 2023

An efficient PdII- and RhIII-controlled site-selective C-H bond alkynylation of imidazopyridines using (bromoethynyl)triisopropylsilane is disclosed. The divergent methodology allows straightforward access to a wide range products alkynylated at the C3 ortho positions. This strategy suggestive practical platform that can be suitable for late-stage diversification may assist in design more selective complementary catalytic systems.

Язык: Английский

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