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Updated: Aug 2, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
One-pot synthesis of polyfunctionalized cyclic urea derivatives
Stefania Fioravanti1, Fabio Marchetti, Alberto Morreale
1Dipartimento di Chimica dell'Università degli Studi di Roma La Sapienza, P.le Aldo Moro 2, I-00185 Roma, Italy.
Organic Letters
|March 28, 2003
Summary
A new synthetic method efficiently produces imidazolidin-2-ones from beta-keto esters. This reaction uses tert-butyl nosyloxycarbamate and calcium oxide under mild conditions, offering a straightforward route to these valuable compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Imidazolidin-2-ones are important heterocyclic compounds with diverse applications.
- Existing synthetic routes may involve harsh conditions or limited substrate scope.
Purpose of the Study:
- To develop a novel, mild, and efficient method for synthesizing imidazolidin-2-ones.
- To explore the reaction of beta-keto esters with tert-butyl nosyloxycarbamate for imidazolidin-2-one formation.
Main Methods:
- Reaction of beta-keto esters with tert-butyl nosyloxycarbamate.
- Use of calcium oxide as a base.
- Mild reaction conditions.
- Structure elucidation via X-ray crystallography.
Main Results:
- Unexpectedly facile synthesis of imidazolidin-2-ones.
- High yields and mild reaction conditions achieved.
- Confirmation of product structure through X-ray crystallography.
Conclusions:
- A new, convenient method for imidazolidin-2-one synthesis has been established.
- The reaction offers a valuable alternative for accessing imidazolidin-2-one scaffolds.
- The methodology is amenable to further exploration in organic synthesis.
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