One‐Step Synthesis of 3,4‐Disubstituted 2‐Oxazolidinones by Base‐Catalyzed CO<subscript>2</subscript> Fixation and Aza‐Michael Addition.
In: Chemistry - A European Journal, Jg. 25 (2019-08-06), Heft 44, S. 10284-10289
Online
academicJournal
Zugriff:
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 γ‐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. [ABSTRACT FROM AUTHOR]
Titel: |
One‐Step Synthesis of 3,4‐Disubstituted 2‐Oxazolidinones by Base‐Catalyzed CO<subscript>2</subscript> Fixation and Aza‐Michael Addition.
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Autor/in / Beteiligte Person: | Mannisto, Jere K. ; Sahari, Aleksi ; Lagerblom, Kalle ; Niemi, Teemu ; Nieger, Martin ; Sztanó, Gábor ; Repo, Timo |
Link: | |
Zeitschrift: | Chemistry - A European Journal, Jg. 25 (2019-08-06), Heft 44, S. 10284-10289 |
Veröffentlichung: | 2019 |
Medientyp: | academicJournal |
ISSN: | 0947-6539 (print) |
DOI: | 10.1002/chem.201902451 |
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