title: Rational synthesis of AB-type N-substituted core-functionalized naphthalene diimides (cNDIs).
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.
authors.affiliation: †Namur Research College (NARC) and Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Berezin
authors.affiliation: †Namur Research College (NARC) and Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Andrea
authors.initials: A
authors.lastname: Sciutto
authors.affiliation: §Elettra - Sincrotrone Trieste, S.S. 14 Km163.5 in Area Science Park, 34149 Basovizza, Trieste, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Demitri
authors.affiliation: †Namur Research College (NARC) and Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium.|‡Department of Pharmaceutical and Chemical Sciences and INSTM UdR of Trieste, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
authors.forename: Davide
authors.initials: D
authors.lastname: Bonifazi
mesh_terms: D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007094:Imides; D009281:Naphthalenes; C542131:naphthalenediimide