Visible‐Light‐Mediated Synthesis of α‐Ketoamides via Oxidative Amination of 2‐Bromoacetophenones Using Eosin Y as a Photoredox Catalyst DOI

Kaushal Kishor,

Neha Sharma Prabhakar,

Krishna Nand Singh

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(19)

Published: Aug. 29, 2023

An oxidative amination of 2-bromoacetophenones has been accomplished to provide α-ketoamides by using photoredox catalysis with air as oxidant. The reactants are readily accessible, and the method is endowed broad substrate scope good functional group tolerance. practicality approach also shown a gram-scale reaction.

Language: Английский

Recent Advances in the Catalytic Synthesis of α‐Ketoamides DOI

Mathew B. Aaron,

P. Devi, Gopinathan Anilkumar

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides DOI Creative Commons
Shubham Sharma, Dharmender Singh, Sunit Kumar

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 231 - 244

Published: March 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.

Language: Английский

Citations

10
Copper-Catalyzed Synthesis of α-Keto Amides from Sulfoxonium Ylides DOI
Xinghua Wang, Yazhou Li,

Naixuan Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8268 - 8278

Published: May 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.

Language: Английский

Citations

10
Direct Synthesis of α-Ketothioamide Derivatives through a One-Pot Reaction of Sulfur Ylides, Nitrosobenzenes, and Thioacetic Acid DOI

Chaowei Xiang,

Fang Luo, Zheng Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8878 - 8887

Published: June 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.

Language: Английский

Citations

3
Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions DOI Creative Commons
Peter Conen, Michaël A. R. Meier

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100086 - 100086

Published: July 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.

Language: Английский

Citations

3
Multicomponent Reaction of CS2, Amines, and Sulfoxonium Ylides in Water: Straightforward Access to β-Keto Dithiocarbamates, Thiazolidine-2-thiones, and Thiazole-2-thiones DOI
Naveen Kumar, Ajay Sharma, Upendra Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6120 - 6125

Published: April 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.

Language: Английский

Citations

9
I2-Mediated Site-Selective C–H Functionalization: Access to p-Amino-Substituted Unsymmetrical Benzils and Quinoxalines from Sulfoxonium Ylides DOI

Rahul Kumar Saini,

Paran J. Borpatra,

Trayambek Nath Chaubey

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5536 - 5545

Published: April 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.

Language: Английский

Citations

3
Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives DOI Creative Commons

Gurupada Hazra,

Ahmad Masarwa

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6396 - 6400

Published: Aug. 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.

Language: Английский

Citations

7
Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage DOI

Mahesh Kumar,

Anup Sharma,

Km Ishu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 9888 - 9895

Published: June 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.

Language: Английский

Citations

2
Metal-free oxidative coupling of aryl acetylene with elemental sulphur and amines: A facile access to α-ketothioamides DOI
Deepika Sharma, Rana Chatterjee, V. Dhayalan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5913 - 5917

Published: Jan. 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

Language: Английский

Citations

2