Oxidative Free-Radical C(sp²)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8521 - 8530

Опубликована: Июнь 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Язык: Английский

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Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation

Synthesis, Год журнала: 2024, Номер 56(16), С. 2565 - 2571

Опубликована: Апрель 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Язык: Английский

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Fe(OTf)₃-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(17), С. 4298 - 4304

Опубликована: Янв. 1, 2023

This method involves a cascade reaction utilizing 1 and enamines 2 as substrates, which occurred by refluxing mixture of the starting materials in toluene with catalyst Fe(OTf) 3 .

Язык: Английский

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Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11627 - 11636

Опубликована: Авг. 9, 2023

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)-H bond functionalization/C(sp3)-O cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction 1,4-DHPs by using esters as C4 sources, well expands application in heterocycle synthesis.

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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Copper-Catalyzed Oxidative [3 + 2] Cycloaddition of Enamines and Pyridotriazoles toward Indolizines

Organic Letters, Год журнала: 2024, Номер 26(6), С. 1249 - 1254

Опубликована: Фев. 2, 2024

An efficient copper catalytic system has been established for the synthesis of highly functional indolizines through oxidative [3 + 2] cycloaddition enamines and pyridotriazoles. This modular platform is compatible with a broad range groups, including natural complex skeletons, allowing late-stage modifications. It features step-economical, regioselective, easy-handling procedure applied in constructing small molecules potent activity toward inhibiting VEGF–NRP1 interaction one-pot reaction pyridotriazoles, amines, aldehydes.

Язык: Английский

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A simple, facile and greener route to thiazolo[3,2- c ]pyrimidinones in semi-aqueous medium and their antibacterial properties

Synthetic Communications, Год журнала: 2024, Номер 54(6), С. 491 - 503

Опубликована: Фев. 10, 2024

By using easily accessible heterocyclic enamines, acetaldehyde (or formaldehyde) and primary amines as suitable precursors, a water-assisted three-component synthesis of new 3-oxothiazolo[3,2-c]pyridimines has been efficiently achieved in mild semi-aqueous medium. All the cyclization reactions under optimized catalyst-free conditions furnish target compounds 40–100% yields. Although cyclizations with arylamines presence formaldehyde yield moderate to good yields, certain involving aryl do not result any product formation. Structural characterization all products were performed by means FT-IR,1H 13C NMR HRMS analyses. Besides, some demonstrated bacteriostatic effects antibacterial study conducted against S. aureus epidermidis bacteria.

Язык: Английский

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PIFA-mediated room temperature dehydrogenative annulation for the synthesis of 2-alkenyl oxazoles

Journal of Molecular Structure, Год журнала: 2024, Номер 1308, С. 138142 - 138142

Опубликована: Март 24, 2024

Язык: Английский

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Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(19), С. 4139 - 4144

Опубликована: Июль 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

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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