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

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

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I₂-Promoted Chemoselective Annulative Coupling of 2-Aminobenzamides with Sulfoxonium Ylides: Easy Access to Quinazolinones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12410 - 12420

Published: Aug. 20, 2024

A flexible and metal-free synthetic approach for synthesizing 2-benzoyl quinazolinones 2-aryl via molecular iodine-mediated annulative coupling of sulfoxonium ylides with 2-aminobenzamides has been disclosed. The method demonstrates remarkable chemoselectivity efficiency, leading to high yields under optimized conditions. broad substrate scope, scalability, practical utility were highlighted through diverse applications, including gram-scale reactions the synthesis biologically significant compounds such as tryptanthrin chemo/biosensor derivative.

Language: Английский

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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

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(17), P. 2029 - 2034

Published: April 29, 2024

Comprehensive Summary A [2 + 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 I 2 –DMSO‐meditated process, C—NO bond nitroacetate is cleaved, affording a C1 synthon, formation two C—C C—N bonds quaternary carbon center are constructed in one pot. This method good substrate compatibility permits late‐stage modification pharmaceutical compounds.

Language: Английский

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

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 21, 2024

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

Language: Английский

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