BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. H-1 NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed. (C) 2015 Elsevier B.V. All rights reserved.