Mild, convenient and versatile Cu-mediated synthesis of N-aryl-2-imidazolidinones
A mild, general, convenient and practical methodology for the selective copper-mediated mono N-arylation of unprotected 2-imidazolidinone was developed. Strong electron-donating groups and free hydroxy and amino groups on the aryl iodide substrates were well tolerated. The use of n-butanol as the solvent for the copper-catalysed mono-arylation of 2-imidazolidinone is unprecedented.
Preparation of N-substituted imidazolidinones and N-substituted 2-thionimidazolidinones
The invention is a process for the preparation of N-substituted imidazolidinones and N-substituted 2-thionimidazolidinones which comprises contacting an oxazolidinone with a compound containing a nitrogen directly bonded to a carbonyl or a thiocarbonyl group in the presence of a Lewis acid catalyst or the hydrate of a Lewis acid catalyst under conditions such that an N-substituted imidazolidinone or N-substituted 2-thionimidazolidinone is prepared. The compound containing a nitrogen directly bonded to a carbonyl or a thiocarbonyl group is an isocyanate or isothiocyanate or a compound wherein the nitrogen is reactive and the carbonyl or thiocarbonyl group is further bonded to a substituent by a bond which is clevable under the reaction conditions. The Lewis acid catalyst corresponds to the formula wherein M is a group IB-VIIIB, IIIA or IVA element with the proviso that M is not C or Si; X is a halogen; and n is 2, 3 or 4.
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(2008/06/13)
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