One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones.

doi:10.1039/c8ob03111h

Paper

One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones.

Published Mar 13, 2019 · Jia-Yun Haung, Indrajeet J. Barve, Chung‐Ming Sun

Organic & biomolecular chemistry

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7

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1

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Abstract

A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones.

Study Snapshot

This study presents a new one-pot method for the synthesis of substituted 4-arylidene imidazolin-5-ones from amino acid esters, isocyanates, and -bromoketones, with potential applications in the synthesis of 2-iminothiazolines and 2-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones.

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References

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This one-pot synthesis method allows for large-scale access to C2-arylated or alkenylated imidazolone-based green fluorescent protein (GFP) and Kaede protein fluorophores, with flexible electronic group introduction.

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The red chromophore of Kaede, a green-to-red photoconvertible fluorescent protein, can be synthesized using natural amino acid residues, potentially diversifying posttranslational chemistry in GFP-like proteins.

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Highly fluorescent GFP-chromophore analogues, 1a-h, were successfully synthesized, offering potential as probes and enabling the study of biomolecules.

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Citations

New imidazole-2-ones and their 2-thione analogues as anticancer agents and CAIX inhibitors: Synthesis, in silico ADME and molecular modeling studies.

New imidazole-2-ones and their 2-thione analogues show potential as anticancer agents and CAIX inhibitors, with the 4b compound showing the highest biological activity.

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Ultrasound-assisted methodology efficiently synthesizes biologically important 2-iminothiazolines, showing potential as antimicrobials, with moderate activity against both Gram positive and Gram negative bacteria.

Adaptation Strategies to Improve the Resistance of Oilseed Crops to Heat Stress Under a Changing Climate: An Overview

Adaptation strategies using CRISPR/Cas genome editing and OMICS technology can enhance heat stress tolerance in oilseed crops, reducing seed and oil yield losses in the face of climate change.

An Overview of the One-pot Synthesis of Imidazolines

One-pot syntheses are a simple, efficient, and eco-friendly method for synthesising organic compounds, minimizing reaction time, separation procedures, and ecological impact.