Synthesis and thermal transformations of spiro-fused N-phthalimidoaziridines |
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Authors: | Alena S Pankova Mikhail A Kuznetsov |
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Institution: | Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russia |
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Abstract: | Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3-diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiroaziridine-2,2′-indene]-1′,3′-diones in good yields. Heating these aziridines with standard dipolarophiles (N-phenylmaleimide, dimethyl acetylenedicarboxylate, maleate, and fumarate) leads, in most cases, to spiroinden-2,2′-pyrrole] derivatives as products of 1,3-dipolar cycloaddition of the intermediate azomethine ylides with up to 70–95% yields in the case of N-phenylmaleimide. As is typical for 2-acylaziridines, the competing rearrangement into 2-aryl-4H-indeno2,1-d]1,3]oxazol-4-ones prevails for less active dipolarophiles. Increasing the electron-releasing properties of the 3-aryl ring allows the observation of the push–pull effect of electron-donating and electron-withdrawing substituents on the ease of the three-membered ring-opening. |
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Keywords: | Aziridine Azomethine ylide 1 3-Dipolar cycloaddition Indene-1 3-dione Spiro compounds |
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