Imidazolidin-4-ones via (3+2) cycloadditions of aza-oxyallyl cations onto (E)-N-arylideneanilines

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Date: Oct. 10, 2018
From: Tetrahedron Letters(Vol. 59, Issue 41)
Publisher: Elsevier B.V.
Document Type: Report
Length: 259 words

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Abstract :

To access, purchase, authenticate, or subscribe to the full-text of this article, please visit this link: http://dx.doi.org/10.1016/j.tetlet.2018.08.056 Byline: Oznur Eyilcim (a), Sezin Issever (a), Nuket Ocal (a,*), Scott Gronert (b,*), Ihsan Erden [ierden@sfsu.edu] (c,*) Keywords Aza-oxyallyl; Aza-cyclopropanone; N-arylimine; (3+2) cycloaddition; Imidazolidin-4-one Highlights * A new trapping method for aza-oxyallyl cations is described. * Aza-oxyallyl cations undergo novel (3+2) cycloadditions onto N-arylimines. * The products from these reactions are imidazolidin-4-ones. * The reactions are regioselective and in most cases stereoselective. * Experimentally observed regioselectivities are confirmed by DFT calculations. 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 NEt.sub.3, 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+G.sup.** 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. Author Affiliation: (a) Department of Chemistry, Faculty of Arts and Sciences, Yildiz Technical University, Davutpasa Campus, 34220 Esenler, Istanbul, Turkey (b) Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond, VA 23284, USA (c) Department of Chemistry and Biochemistry, San Francisco State University, 1600 Holloway Avenue, San Francisco, CA 94132, USA * Corresponding authors. Article History: Received 31 July 2018; Revised 24 August 2018; Accepted 28 August 2018

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Gale Document Number: GALE|A554472412