Imidazolidin-4-ones via (3+2) cycloadditions of aza-oxyallyl cations onto (E)-Narylideneanilines
Oznur Eyilcim1, Sezin Issever1, Nuket Ocal1
1Department of Chemistry, Faculty of Arts and Sciences, Yildiz Technical University, Davutpasa Campus, 34220 Esenler-Istanbul, Turkey.
Abstract:
In the course of our studies on the chemistry of oxyallyl species we uncovered a new (3+2) cycloaddition of aza-oxyallyl systems, generated in situ from N-benzyloxy-2-chloroamides in the presence of NEt3, onto N-arylimines yielding imidazolidin-4-ones in moderate to good yields. The cycloadditions are regioselective. Computational modelling using DFT at the M062×/6-311+G** level is in support the observed regioselectivities. Although the path to the trans imidazolin-4-one is favored, the cis product is preferred by almost 8 kcal/mol and could be formed by base-catalyzed epimerization. All products were isolated by chromatography and characterized by means of their FTIR, NMR and HRMS data.
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