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Aromatization Of IMDAF Adducts In Aqueous Alkaline Media

F. Zubkov, Inga K. Airiyan, Julya D. Ershova, T. Galeev, V. P. Zaytsev, E. Nikitina, A. V. Varlamov
Published 2012 · Chemistry

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In this paper, we propose a simple synthesis of isoindoline-4-carboxylic acids by means of the aromatization of 3a,6-epoxyisoindoles in alkaline media. The method is facile from an experimental point of view: a short-term (0.5–2h) reflux of epoxyisoindoles in 5% aqueous solutions of alkali leads to the target products in 40–90% yields. The absence of by-products, ease of isolation of the target products and applicability to acidophobic group bearing substrates favorably distinguishes the proposed procedure from previously utilized acid-catalyzed methods. The proposed strategy has been successfully utilized for isoindole containing compounds and nuevamine-type alkaloids.
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