Ahrens, Lukas
[Author];
Maier, Steffen
[Author];
Misselwitz, Erik
[Author];
Oeser, Thomas
[Author];
Rominger, Frank
[Author];
Freudenberg, Jan
[Author];
Bunz, Uwe H. F.
[Author]
TIPS-Ethynylated naphthodiquinoline and naphthodiacridine
Description:
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.