A Metal-free Synthesis of N-Alkyl-4-vinyl Oxazolidinones
Authors:
- 28 April 2026
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 58 (17) , 2019-2022
Abstract
We report a metal-free synthesis of N-alkyl-4-vinyl oxazolidinones. In the presence of sodium hydride, 4-chloro-1-hydroxy-2-butene reacts efficiently with N-alkyl carbamoylimidazoles to give carbamate intermediates, which undergo a subsequent SN2′ ring closure, providing the N-alkyl-4-vinyl oxazolidinones in high yield on a gram scale. Received: 05 March 2026 Accepted after revision: 10 April 2026 Article published online: 28 April 2026 © 2026. Thieme. All rights reserved. Georg Thieme Verlag KG Oswald-Hesse-Straße 50, 70469 Stuttgart, GermanyKeywords
Funding Information
- Division of Chemistry (CHE-2452977)
This publication has 21 references indexed in Scilit:
- N-Alkyl Carbamoylimidazoles as Isocyanate Equivalents: Exploration of the Reaction Scope for the Synthesis of Ureas, Hydantoins, Carbamates, Thiocarbamates, and OxazolidinonesThe Journal of Organic Chemistry, 2022
- Room-temperature Formal Aza-Wacker Cyclization through Synergistic Copper/TEMPO-catalyzed Radical RelayACS Catalysis, 2021
- Catalytic Site-Selective Carbamoylation of PyranosidesOrganic Letters, 2021
- Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper CatalysisAngewandte Chemie International Edition, 2019
- Copper‐Catalyzed Intramolecular Oxidative Amination of Unactivated Internal AlkenesChemistry – A European Journal, 2016
- Palladium(II)‐Catalyzed Oxidative Cyclization of Allylic Tosylcarbamates: Scope, Derivatization, and Mechanistic AspectsChemistry – A European Journal, 2012
- Palladium(0)-Catalyzed Reaction of Acidic Anilines with (Z)-2-Butene-1,4-diyl Dicarbonate – Preparation ofN-Aryl-4-vinyloxazolidin-2-onesEuropean Journal of Organic Chemistry, 1999
- DTBB-catalysed lithiation of 4-functionalised 1-chloro-2-butenesTetrahedron, 1996
- Asymmetric Ligands for Transition‐Metal‐Catalyzed Reactions: 2‐Diphenylphosphinobenzoyl Derivatives of C2‐Symmetric Diols and DiaminesAngewandte Chemie International Edition, 1992
- Palladium(0)-catalyzed cyclization of 2-butenylene dicarbamates forming 4-vinyl-2-oxazolidonesTetrahedron Letters, 1987