TIPS‐Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes

The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki‐coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel‐Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS‐ethynyl)‐substituted n...

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Detalles Bibliográficos
Autores principales: Ahrens, Lukas, Maier, Steffen, Misselwitz, Erik, Oeser, Thomas, Rominger, Frank, Freudenberg, Jan, Bunz, Uwe H. F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362069/
https://www.ncbi.nlm.nih.gov/pubmed/33938059
http://dx.doi.org/10.1002/chem.202101246
Descripción
Sumario:The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki‐coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel‐Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS‐ethynyl)‐substituted naphtha[1,8‐gh:5,4‐g′h′]diquinoline and naphtho[1,8‐bc:5,4‐b′c′]diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs.

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