Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Centre for Advanced Materials (CAM), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.
Chemistry. 2021 Jul 21;27(41):10569-10573. doi: 10.1002/chem.202101246. Epub 2021 May 27.
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.
报道了两种二氮杂双并薁的合成。双硼化萘与取代的乙基烟酸盐进行铃木偶联，然后通过分子内傅克酰基化反应环化。得到的二酮与炔基化并还原，得到标题化合物，双（TIPS-乙炔基）取代的萘[1,8-gh：5,4-g'h']二喹啉和萘并[1,8-bc：5,4-b'c']二吖啶。与同系物的非氮杂 analogs 相比，氮的掺入使双并薁相对于氧化更稳定。
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