Recent Advances in the Catalytic Synthesis of α‐Ketoamides

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Апрель 21, 2025

Abstract α ‐Ketoamides are privileged chemical entities featuring a carbonyl group bonded to an amide. Bearing two pronucleophilic and proelectrophilic sites, this structural scaffold exhibits distinct properties unparalleled biological activity. Owing its wide application in medicinal, agricultural, synthetic chemistry, methods for assembling moiety ever‐growing demand. With the increasing focus on green synthesis, traditional routes ‐ketoamides have faded recent years giving rise development of photocatalytic, electrosynthetic, microwave‐assisted catalytic protocols. We hereby provide comprehensive critical summary all advancements witnessed field from 2016 present.

Язык: Английский

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An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 231 - 244

Опубликована: Март 2, 2023

An operationally simple and metal-free approach is described for the synthesis of pyrazole-tethered thioamide amide conjugates. The thioamides were generated by employing a three-component reaction diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, elemental sulfur in single synthetic operation. advantages this developed protocol refer to broad substrate scope, easy perform conditions. Moreover, C-3/5-linked conjugates also synthesized via an oxidative amination carbaldehydes 2-aminopyridines using hydrogen peroxide as oxidant.

Язык: Английский

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Copper-Catalyzed Synthesis of α-Keto Amides from Sulfoxonium Ylides

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8268 - 8278

Опубликована: Май 24, 2023

We here described a method to synthesize α-keto amides from simple sulfoxonium ylides and secondary amines under the catalysis of copper. This transformation involved very clean catalytic system, substrates could be extended aryl, heteroaryl, tert-butyl give diversified with good yields. Additionally, mechanistic studies indicated that α-carbonyl aldehyde might key intermediate in reaction system.

Язык: Английский

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Direct Synthesis of α-Ketothioamide Derivatives through a One-Pot Reaction of Sulfur Ylides, Nitrosobenzenes, and Thioacetic Acid

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8878 - 8887

Опубликована: Июнь 7, 2024

A one-pot approach has been developed for the synthesis of α-ketothioamide derivatives from sulfur ylides, nitrosobenzenes, and thioacetic acid. This protocol is carried out under mild reaction conditions in generally moderate to excellent yields without any precious catalysts, affording with structural diversity. Additionally, a possible mechanism this chemical transformation proposed.

Язык: Английский

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Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions

Tetrahedron Chem, Год журнала: 2024, Номер 11, С. 100086 - 100086

Опубликована: Июль 27, 2024

As a readily available and benign waste product of the petrochemical industry, elemental sulfur displays desirable characteristics as raw material for new processes. Accordingly, use reactant or reagent in synthetic organic chemistry receives continuous interest. The implementation procedures often necessitates presence basic nucleophilic compounds, which are known to serve activators, enabling diverse range transformations. However, underlying mechanisms still poorly understood, even synthetically useful well-established reactions that have been decades. While numerous reviews focus on various types products accessible via involving sulfur, this manuscript will put its emphasis common mechanistic steps these transformations, highlighting discussing studies postulated pathways.

Язык: Английский

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Multicomponent Reaction of CS₂, Amines, and Sulfoxonium Ylides in Water: Straightforward Access to β-Keto Dithiocarbamates, Thiazolidine-2-thiones, and Thiazole-2-thiones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 6120 - 6125

Опубликована: Апрель 5, 2023

Simple, versatile, and catalyst-free synthetic methods for β-keto dithiocarbamates, thiazolidine-2-thiones, thiazole-2-thiones via the multicomponent reaction of CS2, amines, sulfoxonium ylides have been described. The furnished dithiocarbamates in presence CS2 secondary whereas primary amines afforded thiazolidine-2-thiones or after dehydration an acidic environment. With simple procedures, has a wide substrate scope excellent functional group tolerance.

Язык: Английский

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I₂-Mediated Site-Selective C–H Functionalization: Access to p-Amino-Substituted Unsymmetrical Benzils and Quinoxalines from Sulfoxonium Ylides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5536 - 5545

Опубликована: Апрель 3, 2024

An I2-mediated approach for selective C–H functionalization of unprotected aniline derivatives synthesizing benzils and quinoxaline from sulfoxonium ylides has been described. Aniline ornamented with different functional groups showed good compatibility. They afforded the corresponding products moderate to high yields via a mild simple procedure. Finally, we validated practicality this method by scaling up reaction further conversion synthesized into other valuable molecules.

Язык: Английский

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Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives

Organic Letters, Год журнала: 2023, Номер 25(34), С. 6396 - 6400

Опубликована: Авг. 23, 2023

Herein, we report a straightforward practical method for efficiently obtaining diverse range of thiophosphonium salts. This involves the direct coupling commercially available thiols and aldehydes with Ph3P TfOH. The setup is simple carried out in metal-free manner. synthetic utility these salts demonstrated through various examples C-P bond functionalizations, enabling synthesis thioether, deuterated thioester, dithioester derivatives. These products, which serve as valuable building blocks, are obtained high yields.

Язык: Английский

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Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9888 - 9895

Опубликована: Июнь 26, 2024

A new strategy for the synthesis of amides has been developed using sulfur-mediated decarboxylative coupling cinnamic acids with amines via oxidative cleavage C═C bond.

Язык: Английский

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Metal-free oxidative coupling of aryl acetylene with elemental sulphur and amines: A facile access to α-ketothioamides

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(29), С. 5913 - 5917

Опубликована: Янв. 1, 2024

A simple and efficient oxidative coupling of aromatic alkynes with elemental sulphur secondary amines has been reported. The iodine/DMSO system easily promoted the transformations, affording thioglyoxamides

Язык: Английский

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