Synthesis of 1,8-Diazaanthracenes as Building Blocks for Internally Functionalized Aromatic Oligoamide Foldamers - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2014

Synthesis of 1,8-Diazaanthracenes as Building Blocks for Internally Functionalized Aromatic Oligoamide Foldamers

Résumé

The synthesis of a variety of 9-functionalized 1,8-diazaanthracene diesters and amino acids is described. Derivatiza-tion in the 9-position relies on facile reactions performed on the 9-chloro and 9-bromomethyl precursors. This has allowed the incorporation of nucleophilic or sensitive functional groups that otherwise cannot be incorporated under standard methods for synthesizing these compounds. Additionally, the synthesis of the protected amino acids via a high yielding monosaponification and subsequent Curtius rearrangement has been accomplished on multi-gram scale. These units, together with the functionalized derivatives should prove to be useful monomers in the synthesis of aromatic oligoamide foldamers.

Domaines

Chimie organique
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Dates et versions

hal-01509467 , version 1 (18-04-2017)

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Michael L. Singleton, Nicola Castellucci, Stéphane Massip, Brice Kauffmann, Yann Ferrand, et al.. Synthesis of 1,8-Diazaanthracenes as Building Blocks for Internally Functionalized Aromatic Oligoamide Foldamers. Journal of Organic Chemistry, 2014, 79 (5), pp.2115-2122. ⟨10.1021/jo402852m⟩. ⟨hal-01509467⟩

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