Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs)

Andrey A. Berezin, Andrea Sciutto, Nicola Demitri, Davide Bonifazi

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)1870-1873
Number of pages4
JournalOrganic Letters
Volume17
Issue number8
DOIs
Publication statusPublished - 17 Apr 2015

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