Issue 10, 2024

π-Expanded azaullazines: synthesis of quinolino-azaullazines by Povarov reaction and cycloisomerisation

Abstract

Doping and extension of polycyclic aromatic hydrocarbons (PAHs) by simple and efficient synthetic methods is of increased demand for the development of novel and improved organic electronics. Diarylindolizino[6,5,4,3-ija]quinolino[2,3-c][1,6]naphthyridines (quinolino-azaullazines) were prepared by combination of Pd catalyzed cross-coupling with Povarov and cycloisomerisation reactions. The products contain an electron-rich ullazine and an electron-poor quinoline moiety and show intramolecular charge transfer properties that can be tuned by the substitution pattern. The optical properties were studied experimentally and further elaborated by (TD)DFT calculations.

Graphical abstract: π-Expanded azaullazines: synthesis of quinolino-azaullazines by Povarov reaction and cycloisomerisation

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2024
Accepted
02 Feb 2024
First published
14 Feb 2024
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2024,22, 2027-2042

π-Expanded azaullazines: synthesis of quinolino-azaullazines by Povarov reaction and cycloisomerisation

J. Polkaehn, R. Thom, P. Ehlers, A. Villinger and P. Langer, Org. Biomol. Chem., 2024, 22, 2027 DOI: 10.1039/D4OB00091A

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