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Updated: Apr 15, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Rational synthesis of AB-type N-substituted core-functionalized naphthalene diimides (cNDIs)
Andrey A Berezin1, Andrea Sciutto1, Nicola Demitri2
1†Namur Research College (NARC) and Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium.
Abstract:
Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.
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