Investigations into Competitive Cycloaddition/Cyclization or Elimination from 1,1-Dimethyl-propargylcarbamates of Anilines
Régis Delatouche A , Aurélien Lesage A , Floraine Collette B , Valérie Héroguez B and Philippe Bertrand A C
+ Author Affiliations
- Author Affiliations
A Laboratoire Synthèse et Réactivité des Substances Naturelles, Unité Mixte de Recherche, Centre National de la Recherche Scientifique (UMR CNRS) 6514,40 Avenue du Recteur Pineau, 86022, Poitiers cedex, France.
B Laboratoire de Chimie des Polymères Organiques, UMR CNRS 5629, 16 Avenue Pey Berland, 33607, Pessac cedex, France.
C Corresponding author. Email: philippe.bertrand@univ-poitiers.fr
Australian Journal of Chemistry 64(2) 166-173 https://doi.org/10.1071/CH10344
Submitted: 16 September 2010 Accepted: 18 October 2010 Published: 15 February 2011
Abstract
The copper-catalyzed reaction of 1,1-dimethyl-O-propargyl aniline carbamates was studied and revealed the unexpected formation of oxazolidin-2-ones and alkylamines. An in-depth study of the reaction conditions showed that the formation of these products was highly dependent on the solvent, copper catalyst and aniline substituents. The reaction can be oriented towards oxazolidinones in pyridine and alkylamines in ethanol, whereas cycloaddition can be achieved in dry tetrahydrofuran.
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