Imidazolidin-4-ones via (3+2) cycloadditions of aza-oxyallyl cations onto (E)-N-arylideneanilines |
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| Authors: | Oznur Eyilcim Sezin Issever Nuket Ocal Scott Gronert Ihsan Erden |
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| Affiliation: | 1. Department of Chemistry, Faculty of Arts and Sciences, Yildiz Technical University, Davutpasa Campus, 34220 Esenler, Istanbul, Turkey;2. Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond, VA 23284, USA;3. Department of Chemistry and Biochemistry, San Francisco State University, 1600 Holloway Avenue, San Francisco, CA 94132, USA |
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| 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 modeling using DFT at the M062x/6-311+G7 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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| Keywords: | Aza-oxyallyl Aza-cyclopropanone (3+2) cycloaddition Imidazolidin-4-one |
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