Synthesis and thermal transformations of spiro-fused N-phthalimidoaziridines: Dedicated to Professor Armin de Meijere on the occasion of his 75th birthday

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15 Citations (Scopus)

Abstract

Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3- diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-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 spiro[inden-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-indeno[2,1-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. © 2014 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2499-2503
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number15
DOIs
Publication statusPublished - 2014

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