Rational Synthesis of AB-Type N-Substituted Core-Functionalized Naphthalene Diimides (cNDIs)

A. Berezin, A. Sciutto, N. Demitri, D. Bonifazi,
Org. Lett. 2015, 17, 1870-1873
DOI: 10.1021/acs.orglett.5b00543


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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