title: Synthesis of 1,8-diazaanthracenes as building blocks for internally functionalized aromatic oligoamide foldamers.
abstract: The synthesis of a variety of 9-functionalized 1,8-diazaanthracene diesters and amino acids is described. Derivatization at 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 a multigram scale. These units, together with the functionalized derivatives, should prove to be useful monomers in the synthesis of aromatic oligoamide foldamers.
authors: University of Bordeaux, CBMN (UMR 5248), Institut Européen de Chimie Biologie, 2 rue Robert Escarpit, 33600 Pessac, France.
authors: Michael L
authors: ML
authors: Singleton
authors: Nicola
authors: N
authors: Castellucci
authors: Stéphane
authors: S
authors: Massip
authors: Brice
authors: B
authors: Kauffmann
authors: Yann
authors: Y
authors: Ferrand
authors: Ivan
authors: I
authors: Huc
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000577:Amides; D000596:Amino Acids; D000873:Anthracenes; D002264:Carboxylic Acids