P(NMe₂)₃-Mediated Regioselective N-Alkylation of 2-Pyridones via Direct Deoxygenation of α-Keto Esters

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3657 - 3665

Опубликована: Фев. 17, 2024

A practical and regioselective direct N-alkylation of 2-pyridones is enabled by use α-keto esters in the P(NMe2)3-mediated deoxygenation process. The reaction proceeds under mild conditions to produce N-alkylated with high selectivity generality, protocol shown be applicable for scale-up synthesis, which makes it promising applications.

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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Cu(II)-NHC Catalyzed Insertion of Quinoid Carbenes into cis-Epoxides: Stereoselective Synthesis of trans-Dihydronaphthodioxine

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

A straightforward synthesis of trans-dihydronaphthodioxine has been efficiently accomplished through Cu(II)-NHC catalysis, involving the stereoselective ring opening cis-epoxides with quinoid-carbene. Intramolecular SN2-like substitution facilitates inversion stereochemistry during cis-epoxide opening. This reaction developed under simple conditions, demonstrating a broad substrate scope wide chemoselective profile. Additionally, late-stage functionalization complex bioactive molecules successfully achieved.

Язык: Английский

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Efficient Synthesis of O-Aryl Esters Using a Recyclable MWCNTs-MNPs/Met-NiCl2 Nanocatalyst in Ionic Liquid

Journal of Inorganic and Organometallic Polymers and Materials, Год журнала: 2025, Номер unknown

Опубликована: Май 19, 2025

Язык: Английский

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Iridium/palladium dual photocatalysis for oxidative decarboxylative esterification of alcohols using α-keto acids

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Herein, we report an unprecedented oxidative decarboxylative C–O cross-coupling reaction for the esterification of feedstock α-keto carboxylic acids and alcohols under mild conditions.

Язык: Английский

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Regioselective ortho C–H insertion of N-nitrosoanilines with naphthoquinone carbenes

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(37), С. 7525 - 7529

Опубликована: Янв. 1, 2023

A Rh( iii )-catalyzed ortho C–H insertion of N -nitrosoanilines with naphthoquinone carbenes has been developed, enabling the synthesis biarylamines and their derivatives through diverse elaborations products.

Язык: Английский

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2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(2)

Опубликована: Ноя. 6, 2023

Abstract 2‐Hydroxypyridines have emerged as versatile nucleophiles in organic synthesis. The N ‐ and O ‐functionalization of 2‐hydroxypyridines affords straightforward practical methods for the construction ‐substituted 2‐pyridones 2‐hydroxypyridines, which are important structural motifs numerous natural products, pharmaceuticals biologically active compounds. Nonetheless, competition between presents an inevitable formidable challenge. In past few decades, chemoselective and/or has received extensive attention from synthetic community, resulting development elegant effective strategies to address this chemoselectivity. This review provides a summary recent advancements realm transition‐metal organo‐catalyzed, well visible‐light promoted functionalization including ‐alkylation, ‐allylation, ‐arylation, ‐alkenylation, ‐alkenylation.

Язык: Английский

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Gold(I)-catalyzed synthesis of N-alkenyl 2-pyridonyl sec-amines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(27), С. 5646 - 5652

Опубликована: Янв. 1, 2024

One-pot gold( i )-catalyzed synthesis was developed in order to prepare N -alkenyl 2-pyridonyl amines. This method provides a series of amines moderate excellent yields (up 98%).

Язык: Английский

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Oxy-pyridinium Ylides Mediated 1,4-Pyridyl/Aryl Translocation

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9852 - 9858

Опубликована: Ноя. 11, 2024

Molecular rearrangement via carbene transfer is a powerful tool to access molecular diversity. Herein, we describe an efficient approach selective pyridyl/aryl relocation rhodium-catalyzed aminoarylation of diazo compounds, providing promising strategy

Язык: Английский

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Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

ChemistrySelect, Год журнала: 2024, Номер 9(45)

Опубликована: Ноя. 30, 2024

Abstract A concise and practicable route to the synthesis of multisubstituted 2‐pyridones via a four‐component one‐pot stepwise cyclization catalyzed by Cs 2 CO 3 has been developed. During this transformation, two new C‐C bonds C‐N were generated through an intermolecular condensation/aza‐Michael reaction/intermolecular Michael addition/intramolecular sequence. The alternative protocol offers complementary provide series structurally diverse polysubstituted (21 examples) in good excellent yields (52–81%) from easily available raw materials arylamines, dialkyl acetylenedicarboxylate, 1,3‐dicarbonyl compounds, trialkyl orthoformate under mild conditions. It might opportunities for discovery 2‐pyridones‐containing drugs.

Язык: Английский

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