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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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Bibliographic Details
Main Authors: Ahrens, Lukas (Author) , Maier, Steffen (Author) , Misselwitz, Erik (Author) , Oeser, Thomas (Author) , Rominger, Frank (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: May 27, 2021
In: Chemistry - a European journal
Year: 2021, Volume: 27, Issue: 41, Pages: 10569-10573
ISSN:1521-3765
DOI:10.1002/chem.202101246
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202101246
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202101246
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Author Notes:Lukas Ahrens, Steffen Maier, Erik Misselwitz, Thomas Oeser, Frank Rominger, Jan Freudenberg, and Uwe H.F. Bunz
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Summary: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.
Item Description:Gesehen am 12.04.2023
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202101246

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