One‐Step Synthesis of 3,4‐Disubstituted 2‐Oxazolidinones by Base‐Catalyzed CO2 Fixation and Aza‐Michael Addition

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Mannisto , J K , Sahari , A , Lagerblom , K , Niemi , T , Nieger , M , Sztanó , G & Repo , T 2019 , ' One‐Step Synthesis of 3,4‐Disubstituted 2‐Oxazolidinones by Base‐Catalyzed CO2 Fixation and Aza‐Michael Addition ' , Chemistry: A European Journal , vol. 25 , no. 44 , pp. 10284-10289 . https://doi.org/10.1002/chem.201902451

Title: One‐Step Synthesis of 3,4‐Disubstituted 2‐Oxazolidinones by Base‐Catalyzed CO2 Fixation and Aza‐Michael Addition
Author: Mannisto, Jere K.; Sahari, Aleksi; Lagerblom, Kalle; Niemi, Teemu; Nieger, Martin; Sztanó, Gábor; Repo, Timo
Contributor: University of Helsinki, Department
University of Helsinki, Department
University of Helsinki, Department
University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
Date: 2019-08-06
Language: eng
Number of pages: 6
Belongs to series: Chemistry: A European Journal
ISSN: 0947-6539
URI: http://hdl.handle.net/10138/324827
Abstract: 2-Oxazolidinones are saturated heterocyclic compounds, which are highly attractive targets in modern drug design. Herein, we describe a new, single-step approach to 3,4-disubstituted 2-oxazolidinones by aza-Michael addition using CO2 as a carbonyl source and 1,1,3,3-tetramethylguanidine (TMG) as a catalyst. The modular reaction, which occurs between a gamma-brominated Michael acceptor, CO2 and an arylamine, aliphatic amine or phenylhydrazine, is performed under mild conditions. The regiospecific reaction displays good yields (av. 75 %) and excellent functional-group compatibility. In addition, late-stage functionalization of drug and drug-like molecules is demonstrated. The experimental results suggest a mechanism consisting of several elementary steps: TMG-assisted carboxylation of aniline; generation of an O-alkyl carbamate; and the final ring-forming step through an intramolecular aza-Michael addition.
Subject: carbon dioxide fixation
cyclization
heterocycles
Michael addition
organocatalysis
CARBON-DIOXIDE
CHEMICAL FIXATION
OXAZOLIDINONES
GUANIDINE
DISCOVERY
ANTIBACTERIAL
OPTIMIZATION
INHIBITORS
DESIGN
ADDUCT
116 Chemical sciences
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