ZIOC scientists have proposed an effective method for the synthesis of sterically hindered acridines

The processes occurring under photoredox catalysis conditions are currently being actively studied all over the world. Most often they proceed in mild conditions, and are also compatible with most functional groups. Compounds based on acridine have been actively used as photocatalysts in recent years. Similar structures have already proved themselves as important structural fragments of medical preparations and functional materials. Nevertheless, the often rather laborious synthesis of a wide range of acridines does not allow them to be introduced into the wide practice of organic synthesis, medicinal chemistry, and materials science.

Scientists of the Laboratory of Functional Organic Compounds of the Zelinsky Institute are actively developing photoredox-catalyzed organic transformations. In the course of their research, they found that among acridinium photocatalysts, most often the best results were achieved using compounds containing an ortho-substituted aromatic group at the C-9 position of acridine. However, until now there have been no general and simple methods for the preparation of these sterically hindered substances. Our researchers proposed a convenient approach to the synthesis of 9-arylacridines through Negishi cross-coupling catalyzed by nickel complexes. Available substrates are used as starting materials, and the developed method can be successfully scaled up to obtain gram amounts of final structures.

Source:

Kirill A. Zhilyaev, Dmitry L. Lipilin, Mikhail D. Kosobokov, Aida I. Samigullina, Alexander D. Dilman Preparation and Evaluation of Sterically Hindered Acridine Photocatalysts Adv. Synth. Catal., 2022, accepted manuscript. DOI: 10.1002/adsc.202200515.