I2‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones

Saini, Rahul Kumar; Borpatra, Paran J.; Pandey, Satyendra Kumar

doi:10.1002/ejoc.202300693

Cited by 5 publications

(1 citation statement)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Considering the aforementioned findings and previous studies, a plausible mechanism for both transformations is illustrated in Scheme . Initially, the nucleophilic interaction of the α-carbon of β-keto-sulfoxonium ylide 1a with the electrophilic iodine generates the intermediate I . For path (a), the intermediate I is trapped by the p -carbon of 2-aminobenzonitrile 2a via a Friedel–Crafts type reaction to generate intermediate II , which is then transformed to intermediate III with the removal of HI.…”

Section: Resultsmentioning

confidence: 99%

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

Saini,

Borpatra,

Chaubey

et al. 2024

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

An I 2 -mediated approach for selective C−H functionalization of unprotected aniline derivatives for synthesizing benzils and quinoxaline derivatives from sulfoxonium ylides has been described. Aniline derivatives and sulfoxonium ylides ornamented with different functional groups showed good compatibility. They afforded the corresponding products with moderate to high yields via a mild and simple procedure. Finally, we validated the practicality of this method by scaling up the reaction and further conversion of the synthesized derivatives into other valuable molecules.

show abstract

Section: Resultsmentioning

confidence: 99%

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

Saini,

Borpatra,

Chaubey

et al. 2024

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

I₂–DMSO‐Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO₂ Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β‐Pyrrolidinones Derivatives with a Quaternary Center

Yu,

Shen,

Zhou

et al. 2024

Chin. J. Chem.

View full text Add to dashboard Cite

Comprehensive SummaryA [2 + 1 + 1 + 1] cyclization reaction has been developed for the synthesis of multisubstituted β‐pyrrolidinones from commercially available aryl methyl ketones, primary amines, and ethyl nitroacetate. In this I2–DMSO‐meditated process, the C—NO2 bond of ethyl nitroacetate is cleaved, affording a C1 synthon, and the formation of two C—C and two C—N bonds and a quaternary carbon center are constructed in one pot. This method has good substrate compatibility and permits the late‐stage modification of pharmaceutical compounds.

show abstract

The Green Synthesis of 2‐Pyrrolin‐5‐ones from Bio‐renewable Glyoxal, Diketones and Amines

Oyejobi,

Gao,

Wang

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Described herein is an effective and green reaction between diketones, amines and bio‐renewable glyoxal, affording a wide range of 2‐pyrrolin‐5‐ones and releasing water as the only byproduct. The reaction features step‐economy, high efficiency, mild conditions, broad substrate scope, hazardous waste avoiding and easy scale‐up. The further transformation between the products and aldehydes can be potentially applied for fluorescent dye synthesis.

show abstract

I₂‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones

Cited by 5 publications

References 56 publications

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

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

I₂–DMSO‐Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO₂ Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β‐Pyrrolidinones Derivatives with a Quaternary Center

The Green Synthesis of 2‐Pyrrolin‐5‐ones from Bio‐renewable Glyoxal, Diketones and Amines

Contact Info

Product

Resources

About

I2‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones

Cited by 5 publications

References 56 publications

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

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

I2–DMSO‐Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO2 Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β‐Pyrrolidinones Derivatives with a Quaternary Center

The Green Synthesis of 2‐Pyrrolin‐5‐ones from Bio‐renewable Glyoxal, Diketones and Amines

Contact Info

Product

Resources

About

I₂‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones

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

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

I₂–DMSO‐Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO₂ Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β‐Pyrrolidinones Derivatives with a Quaternary Center